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United States Patent Office Patiented July 27, 1965 3,197,523 United States Patent Office Patiented July 27, 1965 ex ..is 2. hydrodealkylating said alkylaromatic compound in the 3,197,523 EAEYATON OF ASKYLAROWATC presence of hydrogen and said catalyst at hydrodealkylat (CO/PUNCS ing conditions, and recovering the desired aromatic com Edward Michake, Cilicage, and Richard E. Ralesci, pound. Wheeling, E., assigners to Universal Gil Products Com A further embodiment of the invention is found in a pany, Des Plaines, ii., a corporation of 3eiaware method for the hydrodealkylation of an alkylaromatic No Drawing. Filed Nov. 3, 1961, Ser, No. 149,890 hydrocarbon which comprises passing an aikylaromatic 7 Cais. (C. 260-672) hydrocarbon to a dealkylation zone containing a catalyst which has been prepared by commingling a compound This application relates to a process for the dealkyla 10 containing a metal of Group IV of the Periodic Table tion of alky substituted aromatic compounds. More par with a refractory oxide, calcining the resultant base, and ticularly the invention is concerned with a process for hy thereafter impregnating said base with an oxide of a metal drodealkylating alkyl substituted aromatic hydrocarbons in of Group VIB of the Periodic Table, hydrodealkylating the presence of a catalytic compositicin of matter. said alkylaromatic hydrocarbon in the presence of hy In recent years the use of aromatic hydrocarbons such 5 drogen and said catalyst at a temperature in the range of as benzene and naphthalene has greatly increased. For from about 1000 to about 1500 F. and at a pressure in example, benzene of a high grade purity is used as an in the range of from about 300 to about 1000 pounds per termediate in the preparation of styrene monomer which square inch, renoving reactor effluent from said dealkyla may be polymerized to form a type of rubber. Also ben tion zone, passing said reactor effluent to a high pressure Zene is used as an intermediate in the preparation of 20 separator wherein said effluent is separated into a hydro phenol, aniline, maleic anhydride, insecticides such as gen-rich gaseous fraction and a liquid hydrocarbon frac DDT and benzene hexachloride, and as intermediates in tion, recycling said hydrogen-rich gaseous fraction to said the preparation of synthetic fibers such as some types of dealkylation zone, passing said liquid hydrocarbon frac nylon. Another relatively important use of benzene is tion to a low pressure separator, removing light hydro as an intermediate in the preparation of detergents such carbons, recycling one portion of the remaining liquid as alkyl-aromatic sulfonates. These latter compounds are hydrocarbon fraction to said dealkylation zone, re prepared by alkylating benzene with a long chain poly cycling a second portion of said liquid fraction to admix mer containing from about 12 to about 15 carbon atoms with said reactor effluent prior to entry into said high or more in the chain. Following the alkylation of the pressure separator, removing the remaining portion of benzene the resultant compound may be sulfonated by 30 said liquid hydrocarbon fraction, fractionating said latter any method well known in the art to produce the corre portion, and recovering the desired aromatic hydrocarbon. sponding sulfonic acids. These acids may then be neu Yet another embodiment of the invention is found in tralized by any basic material such as sodium hydride, a method for the hydrodealkylation of an alkylaromatic potassium hydride, etc., to form the corresponding Sul hydrocarbon which comprises passing an alkylaromatic fonates such as sodium or potassium salt of the alkyl hydrocarbon to a dealkylation zone containing a catalyst aromatic sulfonic acid. Furthermore, naphthalene also which has been prepared by commingling stannic chlo finds a wide variety of uses in the chemical field as an ride with a refractory oxide, calcining the resultant base, intermediate in the preparation of such compounds as and thereafter impregnating said base with an oxide of a phthalic anhydride. metal of Group VIB of the Periodic Table, hydrodeal In view of this increased use of aromatic compounds 40 kylating said alkylaromatic hydrocarbon in the presence of a relatively high degree of purity the present process of hydrogen and said catalyst at a temperature in the is concerned with a method of preparing the same and range of from about 1000 to about 1500 F. and at a involves the introduction of an alkylaromatic compound pressure in the range of from about 300 to about 1000 and particularly an alkylaromatic hydrocarbon into a hy pounds per square inch, removing reactor effluent from drodealkylation zone wherein said hydrocarbon is con 45 said dealkylation Zone, passing said reactor effuent to a tacted with hydrogen in the presence of a catalyst where high pressure separator wherein said effluent is separated by the alkylaromatic hydrocarbon is hydrodealkylated to into a hydrogen-rich gaseous fraction and a liquid hydro form the desired alkylaromatic hydrocarbon, the process carbon fraction, recycling said hydrogen-rich gaseous being described in greater detail in the specification. The fraction to said dealkylation zone, passing said liquid hy catalytic composition of matter which is utilized in the 50 drocarbon fraction to a low pressure separator, removing present process differs from catalytic compositions of mat light hydrocarbons, recycling one portion of the remain ter which have heretofore been utilized and the use of ing liquid hydrocarbon fraction to said dealkylation zone, said catalyst will result in obtaining a greater yield of recycling a second portion of said liquid fraction to ad the desired product than heretofore has been accom mix with said reactor effluent prior to entry into said high plished. 55 pressure separator, removing the remaining portion of It is therefore an object of this invention to provide a said liquid hydrocarbon fraction, fractionating said latter process for the hydrodealkylation of alkyl substiuted aro portion and recovering the desired aromatic hydrocarbon. matic compounds. A specific embodiment of the invention resides in a A further object of this invention is to provide a proc method for the hydrodealkylation of toluene which com ess for the hydrodealkylation of alkylaromatic hydrocar 60 prises passing toluene to a dealkylation zone containing bons to the action of hydrogen in the presence cf a novel a catalyst which is prepared by commingling stannic chlo catalytic composition of matter thereby obtaining the de ride with alumina, calcining the resultant base, and there sired aromatic hydrocarbon in greater quantities. after impregnating said base with chromia, hydrode Taken in its broadest aspect one embodiment of this alkylating said toluene in the presence of hydrogen and invention resides in a method for the hydrodealkylation said catalyst at a temperature in the range of from about of an alkylaromatic compound which comprises passing 1000 to about 1500 F. and at a pressure in the range an alkylaromatic compound to a dealkylation zone con of from about 300 to about 1000 pounds per square inch, taining a catalyst which has been prepared by commin removing reactor effluent from said dealkylation zone, gling a compound containing a metal of Group IV of passing said reactor effluent to a high pressure separator the Periodic Table with a refractory oxide, calcining the 70 wherein said effluent is separated into a hydrogen-rich resultant base, and thereafter impregnating said base with gaseous fraction and a liquid hydrocarbon fraction, re an oxide of a metal of Group VIB of the Periodic Table, cycling said hydrogen-rich gaseous fraction to said de 3,197,523 s: 4. alkylation zone, passing said liquid hydrocarbon fraction matter herein described is normally effected at tempera to a low pressure separator, removing light hydrocarbons, tures ranging from about 1000 to about 1500 F. and recycling one portion of the remaining liquid hydrocar at a pressure in the range of from about 300 to about bon fraction to said dealkylation zone, recycling a second 1000 or more pounds per square inch. Whereas, as here portion of said liquid fraction to admix with said reactor inbefore set forth, the normal procedure is to effect the effluent prior to entry into said high pressure separator, hydrodealkylation process at a temperature ranging from removing the remaining portion of said liquid hydrocar about 1250 to about 1350 F. it has now been found that bon fraction, fractionating said latter portion, and re the reaction will proceed at temperatures in the neighbor covering the desired benzene. hood of about 50 less than hereinbefore employed. Other objects and embodiments referring to alterna 0 While the process of this invention may be effected in tive catalytic compositions of matter and to alternative either a batch type or continuous type operation it is pre feed stocks of alkylaromatic hydrocarbons will be found ferred to utilize the latter method of effecting the process. in the following further detailed description of this An illustration of a continuous type operation is to pass invention. the feed stock comprising an alkyl substituted aromatic As hereinbefore set forth the invention is concerned 5 hydrocarbon into a heater wherein said feed stock is with a process for hydrodealkylating an alkyl substituted i.eated to the desired inlet temperature and thereafter aromatic compound and preferably an alkyl substituted passed to a hydrodealkylation or reaction zone containing aromatic hydrocarbon in a catalytic type operation to a catalytic composition of matter of the type set forth prepare aromatic hydrocarbons which are the desired in this specification. In the hydrodealkylation Zone the product. It has now been discovered that when this proc alkyl substituted aromatic hydrocarbon is dealkylated in ess is effected in the presence of a catalyst which contains the presence of hydrogen and the catalyst. The reactor a metal of Group IV of the Periodic Table and a metal of effluent is continuously withdrawn from the reaction zone Group VI of the Periodic Table composited on a refrac and passed to a high pressure separator.
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