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United States Patent (19) (11) 3,847,801 Moser (45) Nov

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United States Patent (19) (11) 3,847,801 Moser (45) Nov United States Patent (19) (11) 3,847,801 Moser (45) Nov. 12, 1974 54 PROCESS FOR SEPARATING 2,656,395 101953 Benson............................... 260/688 HYDROCARBON 3,366,686 lf 968 Rosenthal et al................... 260/688 3,658,922 4/1972 Drake................................. 260/688 (75) Inventor: William R. Moser, Westfield, N.J. 73) Assignee: Exxon Research Engineering Primary Examiner-Herbert Levine Company, Linden, N.J. Attorney, Agent, or Firm-John Paul Corcoran; Robert J. Baran 22 Filed: Dec. 27, 1972 21 Appl. No. 318,876 57 ABSTRACT A process for the selective separation of constituents (52) U.S. Cl.................................. 2081308, 260/688 contained in a liquid hydrocarbon and chloro substi 5ll Int. Cl............................................. B01d 17100 tuted hydrocarbon mixture, said constituents being 58 Field of Search...................... 260/688; 2081308 paraffins, isoparaffins, naphthenes, olefinic hydrocar bons, aromatics and chlorinated aromatic compounds 56 References Cited by selectively removing one of the constituents UNITED STATES PATENTS through forming nitrated compounds by reacting with NO. 3,379,710 4/1968 Ellis................. ... 260/688 2,478,243 8/1949 Coe et al............................ 260/688 5 Claims, No Drawings 3,847,801 2 PROCESS FOR SEPARATING HYDROCARBON Furthermore, alkylated aromatics reacted with nitric oxide according to the following order: polyalkyl D tri This invention relates to a process for either the sepa alkyl D dialkyl D monoalkyl aromatic. It has further ration or upgrading of various hydrocarbon streams. In been observed that the positional isomers of alkylated one aspect, this invention relates to the use of nitric aromatics react in order of para > ortho D meta. oxide for selectively removing various components Illustrative hydrocarbons include the propanes, bu contained in hydrocarbon mixtures. tanes, hexanes, heptanes, octanes, nonanes, undecanes, In a copending application bearing Ser. No. 318,875 dodecanes and their higher homologs; cyclopropanes, filed Dec. 27, 1972 in the name of W. R. Moser, a pro cyclobutanes, cyclopentanes, cyclohexanes, cyclohep cess is described and claimed for the liquid phase re 10 tanes, cyclooctanes, and their higher cyclic homologs; duction of nitric oxide with a hydrocarbon under mild benzene and its alkyl homologs, toluene, xylene, ethyl noncatalytic conditions. benzene, propylbenzene, tetralin, mesitylene, cumene, The reaction and selectivities of N.O., NO, and NO durene and the like; isomeric alkylated hydrocarbons, with hydrocarbons have been described in the prior art. para-xylene, meta-xylene, ortho-xylene, ethylbenzene; For example, A. V. Topchiev, Nitration of Hydrocar 15 isomeric saturated alkanes, n-hexane, 2,3- bons and Other Organic Compounds, Pergamon Press, dimethylbutane, 2,2-dimethylbutane, 2 New York, 1959, pp. 226-268. W. H. Baum, J. G. Crist methylpentane, 3-methylpentane, n-octane, 2,2,4- and E. V. Nagel, U.S. Pat. No. 3,428,414 Appl. June 2, trimethylpentane, 2,3,4-trimethylpentane, 2,4- 1966; M. Schienbaum, J. Org. Chem., 35,2785 (1970). dimethylhexane, 3-methylheptane and the like; pro 20 pene, butenes, pentenes, cyclohexenes, cycloheptenes, However, the reaction of nitric oxide with liquid cyclooctenes and higher homologs and higher alkylated phase hydrocarbons in the absence of oxidants, cata homologs; aromatic olefins, cis- and trans-stilbene, sty lysts, photo-induction, or other initiating molecules in rene and the like. unknown to those skilled in the art. Furthermore, its The most preferred hydrocarbon compounds for rea selectivity towards reaction with various hydrocarbons 25 sons of availability and ease of NO reduction are those is also unknown. alkylated aromatic hydrocarbons containing 7 to 25 Briefly, the subject invention relates to a process for carbon atoms. the selective separation of constituents contained in a Based upon considerable experimentation, it is possi liquid hydrocarbon and chlorosubstituted hydrocarbon ble to disclose workable and preferred parameters in mixture, said consitituents being paraffins, isoparaffins, 30 terms of volumes of the liquid hydrocarbons that are naphthenes, olefinic hydrocarbons, aromatic and chlo contacted per unit time with the gaseous NO com rosubstituted aromatic compounds, said process com pounds and the ratio of the hydrocarbon to the NO prising the steps of concentration of the effluent in the various streams em 1. Continuously contacting said liquid mixture with anating from stationary sources as well as mobile NO at a temperature and pressure sufficient to 35 SOCeS. cause a reaction with at least one of said constitu The reaction must be run in the presence of a liquid tents contained in said mixture to form a nitrated hydrocarbon such as those enumerated hereinabove. compound; The reaction can be run in the presence of an inert 2. Isolating the nitrated compound resulting in Step gaseous diluent such as nitrogen, neon, argon and the 1 and leaving behind an effluent; 40 like. 3. Successively repeating Steps 1 and 2 until In running these systems, the mole ratio of hydrocar a. the nitrated compound which results is that of bon to nitric oxide will normally range from 500:1 to the particular constituent which has the highest 0.04:1. Lower mole ratios give low rates of reaction order of reacting with said NO, or over the temperatures of 0 to 500°C and are therefore b. the effluent comprises substantially a single, un 45 unsatisfactory. Higher ratios are generally more costly. reacted constituent and recovering the said par Molar volume ratios of 10 to 0.5 volumes of hydrocar ticular constituent by removal from the nitrated bon for each molar volume of nitric oxide give good re compound from Step 3(a) by standard proce sults and are hence preferred. dures, e.g., flash distillation. Higher flow rates may accelerate the rate of reaction This separations process has special advantage since 50 at a given temperature since they may increase the the combustion stack gases from refineries, factories, quantity of NO brought into contact with the hydrocar plants, etc. provide local, cheap sources of nitric oxide. bon substrate. However, flow rates of effluent gases between about It has been discovered that pure NO or its admixture 0.1 to 25 volumes per minute per volume of liquid hy with inert gases reacts with hydrocarbons in the follow 55 drocarbon have been successfully employed while the ing order of decreasing reactivity: olefinic > saturated best results have been obtained with flow rates per unit > alkyl aromatics > unsubstituted aromatic hydrocar time from about 0.5 to 5 volumes per minute per vol bons. The unexpected observation that saturated hy ume of hydrocarbon compound. The flow rate of gases drocarbons react faster than aromatics is of special sig used ordinarily depend upon the quantity of hydrocar nificance. This invention has the further advantage that 60 bon compound, the size of the reactor, the pressure and the reaction of nitric oxide with saturated hydrocar the rate of mixing of liquid and gas phases. bons generally obeys the following order of group reac Utilizing reaction temperatures and reaction times as tivity with respect to carbon-hydrogen bonds: indicated previously, good results have been obtained with reaction temperatures ranging between 0 and 65 500°C. Lower temperatures give little or no reaction particularly with a more sluggishly reactive saturated - l-H>)CH-CH. aliphatic while higher temperatures give rise to com 3,847,801 3 4 pounds which are not particularly desired when the action with alkyl aromatics or aromatics, (e) positional more reactive olefins are used as substrates. The rea isomers of alkylated aromatics at different rates. sonable balance. between reaction rate and quality of product can usually be obtained at temperatures rang EXAMPLE 2 ing between about 100 and 225°C. and for these rea 5 A typical C6-isomerate stream consisting of 0.66 g of sons this represents a preferred operating temperature 2,2-dimethylbutane, 0.23 g of 2,3-dimethylbutane, range. 0.67 g of 2-methylpentane, 0.37 g of 3-methylpentane, The reaction time is a variable dependent upon the and 0.26 g of n-hexane was degassed and heated with acitvity of the particular hydrocarbon compound em nitric oxide at 168°C at an initial pressure of 400 psi. ployed, the mole ratio of nitric oxide to the hydrocar 10 Gas chromatographic analysis of the final mixture bon compound, the nitric oxide pressure over the hy showed that 59.3 percent of the starting hydrocarbons drocarbon, the flow rate, the mixing rate and the reac has been consumed. The relative uncorrected molar tion temperature. Ordinarily the reaction produces mo reactivity ratios for the individual hydrocarbons were lecular nitrogen and organic nitro compounds immedi determined as follows: 2,2-dimethylbutane (1.00), n ately but can require as long as several days when the 5 hexane (1.52), 2-methylpentane (2.63), 3 more recalcitrant paraffins are the substrates. methylpentane (2,69), and 2,3-dimethylbutane (4.26). In order to describe the workings of the invention, A similar competition reaction utilizing equimolar the inventive process is described in the following illus isomeric octanes at 168°C and 100 psi nitric oxide pres trative examples. sure after 28 percent conversion showed the following 20 relative order of molar reactivity: 2,2,4- EXAMPLE trimethylpentane (1.00), n-octane (1.52), 3 The hydrocarbons (0.15 mole) in Table I were, ex methylheptane (2.58), and 2,3,4-trimethylpentane cepting the solid compounds, passed through alumina (3.51). and degassed by the freeze-thaw method. They were Extensive competition experimentation utilizing then placed in a glass autoclave and degassed again at 25 equimolar concentrations of aromatics and saturated 165°C by argon pressurization-depressurization cycles. hydrocarbons at 168°C and 100-300 psi nitric oxide Nitric oxide was pressurized into the reactor several pressure, afforded the following order of reactivity. Iso times to 80 psi; finally the hydrocarbon was then satu propylbenzene was the reference compound and as rated with nitric oxide at a pressure near 80 psi.
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