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United States Patent Office Patented Oct 2,721,885 United States Patent Office Patented Oct. 25, 1955 1. 2 thus a part of a saturated group including an alkyl group 2,721,885 and a cycloalkyl group, and an aralkyl group containing CONDENSATION OF AROMATIC COMPOUNDS no olefinic unsaturation. WITH UNSATURATED ORGANIC COMPOUNDS An object of this invention is to react an unsaturated or N THE PRESENCE OF COMPOSITE CATALYSTS 5 ganic compound with an aromatic compound selected from Herman Pines, Evanston, Ill., and Vladimir N. patieff, the group consisting of carbocyclic and heterocyclic aro deceased, late of Chicago, Ill., by Vladimir Haensel, matic ring compounds having attached to a nuclear carbon Hinsdale, Herman Pines, Evanston, and Vincetta atom a nonolefinic or saturated carbon atom to which is Kibort, Chicago, Ill., executors, assignors to Universal attached at least one hydrogen atom. Oil Products Company, Des Piaines, Ill., a corporation An additional object of this invention is to react a of Delaware monoolefin with an alkylaromatic hydrocarbon to form an aromatic hydrocarbon with a longer alkyl group. No Drawing. Application June 7, 1954, Another object of this invention is to condense ethylene Serial No. 435,031 with the side chain of an alkylaromatic hydrocarbon hav 14 Claims. (C. 260-668) ing attached to a nuclear carbon atom a carbon atom of said alkyl group to which is attached at least one hydro This application is a continuation-in-part of our co gen aton. pending application Serial No. 219,314, filed April 4, 1951, Still another object of this invention is to condense ethyl now abandoned. ene with the alkyl side chain of an alkylbenzene hydro This invention relates to the condensation of unsatu carbon, said side chain containing an alpha carbon atom rated organic compounds with aromatic compounds and to to which is attached a replaceabie hydrogen atom. products formed thereby. This invention relates more par A further object of this invention is to condense ethylene ticularly to the side chain alkylation with an olefin of an with the cycloalkyl group of a cycloalkylbenzene hydro alkylaromatic hydrocarbon in which a carbon atom com carbon, said cycloalkyl group having a hydrogen atom bined with the aromatic nucleus is also combined with 2 combined with the carbon atom of the cycloalkyl group at least one hydrogen atom. The process relates more which is attached to the aromatic ring. specifically to the side chain alkylation with ethylene of A still further object of this invention is to provide a an alkylbenzene hydrocarbon having at least one hydrogen process for the side chain alkylation of an alkylaromatic atom combined with a carbon atom in alpha position to hydrocarbon. the benzene ring. A further object of this invention is to condense ethyl The condensation of aromatic compounds with unsatu ene with a polycyclic hydrocarbon having at least one of rated organic compounds such as the alkylation of aro the rings Saturated and having at least one hydrogen atom matic hydrocarbons with olefinic hydrocarbons, has been combined with the carbon atom of the saturated ring the subject of many investigations over a long period of which is attached to the aromatic ring. time. Many different catalysts have been used including An additional object of this invention is to provide a various mineral acids and acid-acting compounds but in method for producing an aromatic compound containing a all of these reactions, nuclear condensation has always long hydrocarbon side chain, said compound being useful been effected. Thus in the acid catalyzed alkylation of in the production of detergents, wetting agents and the aromatic compounds having attached to a carbon atom of like. the ring a saturated carbon atom to which is attached at 40 One embodiment of this invention relates to a process least one hydrogen atom, the entering alkyl group attaches which comprises reacting a nonconjugated olefinic hydro to the aromatic nucleus. No direct catalytic method of carbon and an aromatic compound selected from the group introducing the alkyl group into the side chain has been consisting of carbocyclic aromatic and heterocyclic aro known. Heretofore we accomplished side chain alkyla matic ring compounds having attached to a nuclear carbon tion of toluene and related alkylaromatic compounds by atom a carbon atom of a hydrocarbon group selected from noncatalyzed thermal means as set forth in our copending the group consisting of an alkyl group, a cycloalkyl group, application Serial Number 152,991 filed March 30, 1950, a cycloalkalkyl group and an aralkyl group and to which now abandoned, but this thermal alkylation process re last named carbon atom is attached at least one hydrogen quires high temperatures and high pressures for its suc atom, the process being carried out at condensation con cessful operation. 50 ditions in the presence of an alkali metal and of an or We have now found that side chain alkylation of toluene ganic compound represented by the formula RX wherein and other carbocyclic aromatic and heterocyclic aromatic R is a member of the group consisting of alkyl, alkenyl, ring compounds having a nonolefinic double bond such cycloalkyl, aralkyl, and aryl radicals and X is selected as pyridine, quinoline, pyrrole, etc. and having attached from the group consisting of a hydroxyl group, a car to a nuclear carbon atom a saturated carbon atom to 55 boxylic acid group, an alkoxyl group, a nitro group, and which is attached at least one hydrogen atom may also a cyano group, and recovering the resultant condensation be used as starting materials to effect side chain alkyla product. tion with an olefin at relatively lower temperatures and A Second embodiment of this invention relates to a pressures in the presence of a catalyst comprising essen process which comprises reacting a nonconjugated olefinic tially an alkali metal and an organic compound repre 60 hydrocarbon and an aromatic compound selected from Sented by the formula RX wherein R is a member of the the group consisting of carbocyclic aromatic and hetero group consisting of alkyl, alkenyl, cycloalkyl, aralkyl and cyclic aromatic ring compounds having attached to a aryl radicals and X is selected from the group consisting nuclear carbon atom a carbon atom of a saturated hydro of a hydroxyl group, a carboxylic acid group, an alkoxyl carbon group and to which last named carbon atom is group, a nitro group and a cyano group. The carbon atom attached at least one hydrogen atom at condensation conditions in the presence of an alkali metal and of an which is attached to the aromatic nucleus of said aromatic organic compound represented by the formula RX where compounds is referred to as a "saturated" carbon atom be in R is a member of the group consisting of alkyl, alkenyl, cause it is a part of a nonolefinic group such as an alkyl cycloalkyl, aralkyl, and aryl radicals and X is selected group, a cycloalkyl group, and an aralkyl group contain from the group consisting of a hydroxyl group, a car ing no ethylenic bonds or similar unsaturation. The car boxylic acid group, an alkoxyl group, a nitro group, and bon atom which is attached to an aromatic nucleus is a cyano group. 2,721,885 3 4. Another embodiment of this invention relates to a proc wherein Ar represents an aromatic radical having a ess which comprises reacting a monoolefin and an aro nucleus selected from carbocyclic and heterocyclic nuclei matic compound having attached to a nuclear carbon and R and R' each separately and independently repre atom a carbon atom of a saturated hydrocarbon group sents a member of the group consisting of a hydrogen and to which last named carbon atom is attached at least 5 atom, an alkyl group, a cycloalkyl group, and an aryl one hydrogen atom at condensation conditions in the group and R and R' together represent a cycloalkyl group, presence of an alkali metal and of an organic compound the process being carried out at a condensation tempera represented by the formula RX wherein R is a member ture in the presence of a catalyst comprising essentially of the group consisting of alkyl, alkenyl, cycloalkyl, an alkali metal and an organic compound represented by aralkyl, and aryl radicals and X is selected from the the formula RX wherein R is a member of the group group consisting of a hydroxyl group, a carboxylic acid consisting of alkyl, alkenyl, cycloalkyl, aralkyl, and aryl group, an alkoxyl group, a nitro group, and a cyano group. radicals and X is selected from the group consisting of a Still another embodiment of this invention relates to hydroxyl group, a carboxylic acid group, an alkoxyl group, a process for producing longer chain aromatic hydrocar a nitro group, and a cyano group, and recovering the re w bons which comprises reacting an alkene and an aromatic Sultant condensation product. hydrocarbon having attached to a nuclear carbon aton Still another embodiment of this invention relates to a carbon atom of a saturated hydrocarbon group and to a process for producing normal propylbenzene which com which last named carbon atom is attached at least one prises reacting ethylene and toluene at a condensation hydrogen atom at a condensation temperature in the temperature in the presence of a catalyst comprising presence of an alkali metal and of an organic compound essentially sodium and an organic hydroxy compound, represented by the formula RX wherein R is a member and recovering the resultant condensation product. of the group consisting of alkyl, alkenyl, cycloalkyl, Another embodiment of this invention relates to a aralkyl, and aryl radicals and X is selected from the process for producing normal propylbenzene which com group consisting of a hydroxyl group, a carboxylic acid prises reacting ethylene and toluene at a condensation group, an alkoxyl group, a nitro group, and a cyano group.
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