Method of making a synthetic alkylaryl compound

Abstract

A process for alkylating an aromatic compound comprising reacting (a) a first amount of at least one aromatic compound with a first amount of a mixture of olefins having from about 8 to about 100 carbon atoms, in the presence of a strong acid catalyst; and reacting the product of (a) with an additional amount of at least one aromatic compound and an additional amount of a strong acid catalyst, and optionally, with an additional amount of a mixture of olefins selected from olefins having from about 8 to about 100 carbon atoms, wherein the resulting product comprises at least about 80 weight percent of a 1,2,4 tri-alkylsubstituted aromatic compound.

1 . An alkylated aromatic compound prepared by a process for alkylating an aromatic compound comprising
 (a) reacting a first amount of at least one aromatic compound with an amount of a mixture of olefins selected from olefins having from about 8 to about 100 carbon atoms, in the presence of a strong acid catalyst; and   (b) reacting the product of (a) with an additional amount of at least one aromatic compound and an additional amount of a strong acid catalyst and, optionally, with an additional amount of a mixture of olefins selected from olefins having from about 8 to about 100 carbon atoms, wherein the resulting product comprises at least about 80 weight percent of a 1,2,4 tri-alkylsubstituted aromatic compound.   
   
   
       2 . The alkylated aromatic compound according to  claim 1  wherein the product of (b) further comprises 1, 2, 3, tri-alkylsubstituted aromatic compound or mixtures thereof. 
   
   
       3 . The alkylated aromatic compound according to  claim 1  wherein the at least one aromatic compound is selected from unsubstituted aromatic compounds, monosubstituted aromatic compounds, and disubstituted aromatic compounds. 
   
   
       4 . The alkylated aromatic compound according to  claim 3  wherein the at least one aromatic compound is selected from benzene, toluene, meta-xylene, para-xylene, ortho-xylene, and mixtures thereof. 
   
   
       5 . The alkylated aromatic compound according to  claim 4  wherein the at least one aromatic compound is selected from meta-xylene, para-xylene, ortho-xylene and mixtures thereof. 
   
   
       6 . The alkylated aromatic compound according to  claim 5  wherein the at least one aromatic compound is ortho-xylene. 
   
   
       7 . The alkylated aromatic compound according to  claim 1  wherein the mixture of olefins in step (a) or step (b) is a mixture of linear olefins, a mixture of linear isomerized olefins, a mixture of branched olefins, a mixture of partially branched olefins, or a mixture thereof. 
   
   
       8 . The alkylated aromatic compound according to  claim 7  wherein the mixture of olefins in step (a) or step (b) is a mixture of linear olefins. 
   
   
       9 . The alkylated aromatic compound according to  claim 8  wherein the mixture of linear olefins is a mixture of normal alpha olefins. 
   
   
       10 . The alkylated aromatic compound according to  claim 9  wherein the mixture of linear olefins comprises olefins derived through cracking of petroleum wax or Fischer Tropsch wax. 
   
   
       11 . The alkylated aromatic compound according to  claim 10  wherein the Fischer Tropsch wax is hydrotreated before cracking. 
   
   
       12 . The alkylated aromatic compound according to  claim 7  wherein the mixture of olefins comprises from about 8 carbon atoms to about 100 carbon atoms. 
   
   
       13 . The alkylated aromatic compound according to  claim 12  wherein the mixture of olefins is derived from linear alpha olefins or isomerized olefins containing from about 8 to 100 carbon atoms. 
   
   
       14 . The alkylated aromatic compound according to  claim 13  wherein the mixture of olefins is derived from linear alpha olefins or isomerized olefins containing from about 10 to about 80 carbon atoms. 
   
   
       15 . The alkylated aromatic compound according to  claim 14  wherein the mixture of olefins is derived from linear alpha olefins or an isomerized olefins containing from about 14 to about 60 carbon atoms. 
   
   
       16 . The alkylated aromatic compound according to  claim 8  wherein the mixture of linear olefins is a mixture of linear internal olefins which have been derived from olefin metathesis. 
   
   
       17 . The alkylated aromatic compound according to  claim 1  wherein the mixture of olefins is a mixture of branched olefins. 
   
   
       18 . The alkylated aromatic compound according to  claim 17  wherein the mixture of branched olefins comprises polyolefin compounds derived from C 3  or higher monoolefins. 
   
   
       19 . The alkylated aromatic compound according to  claim 18  wherein the polyolefin compound is either polypropylene or polybutylene. 
   
   
       20 . The alkylated aromatic compound according to  claim 19  wherein the polyolefin compound is polypropylene. 
   
   
       21 . The alkylated aromatic compound according to  claim 20  wherein the polyolefin compound is polybutylene. 
   
   
       22 . The alkylated aromatic compound according to  claim 1  wherein the strong acid catalyst is selected from the group consisting of hydrochloric acid, hydrofluoric acid, hydrobromic acid, sulfuric acid, perchloric acid, trifluoromethanesulfonic acid, fluorosulfonic acid, and nitric acid. 
   
   
       23 . The alkylated aromatic compound according to  claim 22  wherein the strong acid catalyst is hydrofluoric acid. 
   
   
       24 . The alkylated aromatic compound according to  claim 1  wherein the strong acid catalyst may be recycled. 
   
   
       25 . The alkylated aromatic compound according to  claim 1  wherein the reaction takes place in a continuous process. 
   
   
       26 . The alkylated aromatic compound according to  claim 1  wherein, in step (b), the product of step (a) is reacted with an additional amount of at least one aromatic compound and an additional amount of a mixture of olefins selected from olefins having from about 8 to about 100 carbon atoms. 
   
   
       27 . The alkylated aromatic compound according to  claim 1  wherein the resulting product comprises at least about 85 weight percent of a 1,2,4 tri-alkylsubstituted aromatic compound.