Process for separating linear alpha olefins from a crude stream containing saturated hydrocarbons, Internal olefins, branched olefins, and linear alpha olefins

Abstract

This invention relates to a process for separating and isolating saturated hydrocarbons from olefins, and in particular, to a process for separating and isolating saturated hydrocarbons from olefins in a Fisher-Tropsch stream. There is provided a process for separating olefins from saturated hydrocarbons in a feedstock, comprising: a) contacting a feedstock comprising olefins and saturated hydrocarbons, such as paraffins, with a linear polyaromatic compound under conditions effective to form a reaction mixture comprising linear polyaromatic compound-olefin adducts and saturated hydrocarbons; b) separating the linear polyaromatic compound-olefin adducts from the saturated hydrocarbons in the reaction mixture to form a saturated hydrocarbon stream and an adducted olefin stream; c) dissociating the linear polyaromatic compound-olefin adducts to form linear polyaromatic compounds and an olefin composition; and optionally d) separating the linear polyaromatic compound formed in step c) from the olefin composition; whereby the olefin composition is enriched in the concentration of olefins over the concentration of olefins in the feedstock and the saturated hydrocarbon stream is enriched in saturated hydrocarbons over the concentration of saturated hydrocarbons in the feedstock.

What we claim is:  
     
         1 . A process for treating a feedstock composition comprising linear alpha olefins, internal olefins, and saturated hydrocarbons, comprising: 
 a) contacting the feedstock composition with a linear polyaromatic compound in a first reaction zone under conditions effective to form a reaction mixture comprising linear polyaromatic compound-olefin adducts and saturated hydrocarbons;    b) separating the first linear polyaromatic compound-olefin adducts from the saturated hydrocarbons in the reaction mixture to form a first adducted olefin stream and a saturated hydrocarbon stream;    oi) dissociating linear polyaromatic compound-olefin adducts in the first adducted olefin stream to form linear polyaromatic compounds and an olefin composition comprising alpha olefins and internal olefins;    oii) contacting the olefin composition with linear polyaromatic compounds in an AO reaction zone under conditions effective to form a reaction mixture comprising linear polyaromatic compound-linear alpha olefin adducts and an internal olefin composition;    oiii) separating the linear polyaromatic compound-linear alpha olefin adducts from the reaction mixture obtained from the AO reaction zone to form a linear alpha olefin adducted stream and an internal olefin stream; and    oiv) dissociating the linear polyaromatic compound-linear alpha olefin adducts in the linear alpha olefin adducted stream to form linear polyaromatic compounds and a linear alpha olefin composition;    whereby the concentration of linear alpha olefins in the linear alpha olefin composition is enriched over the concentration of linear alpha olefins in the olefin composition, and the concentration of linear alpha olefins in the olefin composition is enriched over the concentration of linear alpha olefins in the feedstock.    
     
     
         2 . The process of    claim 1   , wherein the feedstock is contacted with a linear polyaromatic compound at a temperature ranging from 150° to about 290° C.  
     
     
         3 . The process of    claim 2   , wherein the feedstock is contacted with linear polyaromatic compound at a temperature ranging from about 240° to about 265° C.  
     
     
         4 . The process of    claim 1   , wherein the molar ratio of olefins in the feedstock to linear polyaromatic compounds ranges from 0.25:1 to 10:1.  
     
     
         5 . The process of    claim 1   , wherein the linear polyaromatic compound-olefin adduct is dissociated by heating the linear polyaromatic compound-olefin adduct to a temperature ranging from about 200° C. to 500° C..  
     
     
         6 . The process of    claim 5   , wherein the linear polyaromatic compound-olefin adduct is heated to a temperature ranging from about 300° C. to 350° C.  
     
     
         7 . The process of    claim 1   , wherein the linear polyaromatic compound formed in step oi) is separated from the olefin composition by vacuum or flash distillation.  
     
     
         8 . The process of    claim 1   , wherein the feedstock comprises a stream derived from a Fisher-Tropsch process.  
     
     
         9 . The process of    claim 8   , wherein the feedstock comprises from 15 wt. % to 70 wt. % olefin, based on the weight of all ingredients in the feedstock.  
     
     
         10 . The process of    claim 9   , wherein the feedstock comprises from 15 wt. % to 65 wt. % linear alpha olefin, based on the weight of all ingredients in the feedstock.  
     
     
         11 . The process of    claim 10   , wherein the feedstock comprises from 5 wt. % to 65 wt. %. paraffin, based on the weight of all ingredients in the feedstock.  
     
     
         12 . The process of    claim 11   , wherein the amount of all olefins in the feedstock other than linear alpha olefins ranges from 5 wt. % to 45 wt. %, based on the weight of all ingredients in the feedstock.  
     
     
         13 . The process of    claim 1   , wherein the amount of all olefins other than linear alpha olefins in the feedstock ranges from 5 wt. % to 45 wt. %, based on the weight of all ingredients in the feedstock.  
     
     
         14 . The process of    claim 13   , wherein the feedstock comprises paraffins in an amount ranging from 5 wt. % to 65 wt. %.  
     
     
         15 . The process of    claim 14   , wherein the amount of paraffin ranges from 65 to 95 wt. % of all ingredients in the feestock.  
     
     
         16 . The process of    claim 1   , wherein the feedstock comprises oxygenates and aromatics collectively present in the feedstock in an amount ranging from 5 wt. % to 40 wt. %.  
     
     
         17 . The process of    claim 1   , wherein the average carbon number of the feedstock ranges from C 5 -C 20  and wherein the predominant olefin species in the feedstock is within said range, inclusive.  
     
     
         18 . The process of    claim 17   , wherein the average carbon number of the feedstock ranges from C 6 -C 18  and wherein the predominant olefin species in the feedstock is within said range, inclusive.  
     
     
         19 . The process of    claim 1   , wherein the linear polyaromatic compound has a greater selectivity for linear alpha olefin compounds over other olefins in an amount of greater than 1:1 by mole.  
     
     
         20 . The process of    claim 19   , wherein the linear polyaromatic compound has a greater selectivity for linear alpha olefin compounds over other olefins in an amount of 2:1 by mole or greater.  
     
     
         21 . The process of    claim 1   , wherein the linear polyaromatic compound comprises substituted or unsubstituted anthracene and/or benzanthracene.  
     
     
         22 . The process of    claim 1   , wherein the linear polyaromatic compound comprises unsubstituted anthracene.  
     
     
         23 . The process of    claim 1   , wherein the rate of olefin recovery from the feedstock ranges from 0.10 to 0.4 moles/unit time based on a feedstock rate of 1.0 moles/unit time.  
     
     
         24 . The process of    claim 1   , wherein the recovery of olefins from the feedstock ranges from 70 to 100*i.  
     
     
         25 . The process of    claim 1   , wherein the rate of linear alpha olefin recovery in step oiii) ranges from 60% to 95%, based on the amount of alpha olefin present in the feedstock.  
     
     
         26 . The process of    claim 1   , wherein the total concentration of olefins and the concentration of linear alpha olefins are enriched in the olefin composition over the concentration of olefins and linear alpha olefins in the feedstock stream, and the concentration of saturated hydrocarbons are reduced in the olefin composition over the concentration of saturated hydrocarbons in the feedstock stream.  
     
     
         27 . The process of    claim 1   , wherein the saturated hydrocarbon stream in enriched in its concentration of saturated hydrocarbons over the concentration over the concentration of saturated hydrocarbons in the feedstock stream.  
     
     
         28 . The process of    claim 27   , wherein the saturated hydrocarbon stream comprises linear alpha olefins, and wherein the concentration of linear alpha olefins in the saturated hydrocarbon stream are reduced in one pass by at least 40% over the concentration of linear alpha olefins present in the feedstock stream.  
     
     
         29 . The process of    claim 27   , wherein the concentration of saturated hydrocarbon in the saturated hydrocarbon stream is enriched by 100% to 400% over the concentration of saturated hydrocarbon in the feedstock stream.  
     
     
         30 . The process of    claim 1   , wherein the concentration of saturated hydrocarbons in the olefin composition is reduced in one pass by at least 90% over the concentration of saturated hydrocarbon in the feedstock.  
     
     
         31 . The process of    claim 30   , wherein the concentration of saturated hydrocarbons in the olefin composition is reduced in one pass by 100% over the concentration of saturated hydrocarbon in the feedstock.  
     
     
         32 . The process of    claim 1   , wherein the concentration of linear alpha olefins present in the olefin composition is enriched by at least 30% over the concentration of linear alpha olefins present in the feedstock composition.  
     
     
         33 . The process of    claim 32   , wherein the concentration of linear alpha olefins present in the olefin composition is enriched by at least 40% over the concentration of linear alpha olefins present in the feedstock composition.  
     
     
         34 . The process of    claim 1   , wherein the concentration of all olefins in the olefin composition is enriched by at least 40% over the concentration of all olefins in the feedstock.  
     
     
         35 . The process of    claim 34   , wherein the concentration of all olefins in the olefin composition is enriched by at least 60% over the concentration of all olefins in the feedstock.  
     
     
         42 . The process of    claim 1   , wherein the feedstock consists essentially of saturated hydrocarbons and olefins, and the concentration of olefins in the olefin composition ranges from 90% to 100%.  
     
     
         43 . The process of    claim 1   , wherein the concentration of linear alpha olefins in the linear alpha olefin composition is enriched by at least 15% over the concentration of linear alpha olefins present in the olefin composition.  
     
     
         44 . The process of    claim 1   , wherein the concentration of linear alpha olefins in the linear alpha olefin composition is enriched by at least 20% over the concentration of linear alpha olefins present in the olefin composition.  
     
     
         45 . The process of    claim 1   , wherein the concentration of linear alpha olefins in the linear alpha olefin composition is enriched by at least 30% over the concentration of linear alpha olefins present in the olefin composition.  
     
     
         46 . The process of    claim 1   , wherein the concentration of all blefins other than linear alpha olefins in the linear alpha olefin composition are reduced by at least 20% over the concentration of linear alpha olefins present in the olefin composition.  
     
     
         47 . The process of    claim 1   , wherein the concentration of internal olefins in the internal olefin stream is enriched over the concentration of internal olefins in the olefin composition.  
     
     
         48 . The process of    claim 1   , wherein the concentration of internal olefins in the internal olefin stream is enriched by at least 15% over the concentration of internal olefins in the olefin composition.  
     
     
         49 . The process of    claim 1   , wherein the concentration of branched olefins in the internal olefin stream is enriched by at least 50% over the concentration of branched olefins in the olefin composition.  
     
     
         50 . The process of    claim 1   , wherein the feedstock comprises a single carbon cut composition.  
     
     
         51 . The process of    claim 50   , wherein the feedstock comprises a single cut C 6 , C c , or C 10 , composition.  
     
     
         52 . A process for contacting a linear polyaromatic compound with a feedstock composition comprising linear alpha olefins, internal olefins, and saturated hydrocarbons, separating the olefins from the saturated hydrocarbons in the feedstock composition to form an olefin composition and a saturated hydrocarbon stream, subsequently contacting a linear polyaromatic compound with the olefin composition comprising linear alpha olefins and internal olefins, and separating the linear alpha olefins from the internal olefins to form a linear alpha olefin stream, whereby the concentration of linear alpha olefins in the linear alpha olefin stream is enriched over the concentration of linear alpha olefins in the feedstock and in the olefin composition.  
     
     
         53 . The process of    claim 52   , wherein the average carbon number of the feedstock ranges from C 5 -C 20  and wherein the predominant olefin species in the feedstock is within said range, inclusive.  
     
     
         54 . The process of    claim 53   , wherein the average carbon number of the feedstock ranges from C 6 -C 18  and wherein the predominant olefin species in the feedstock is within said range, inclusive.  
     
     
         55 . The process of    claim 53   , wherein the linear polyaromatic compound comprises substituted or unsubstituted anthracene or benzanthranene.  
     
     
         56 . The process of    claim 54   , wherein the feed comprises a Fisher-Tropsch stream.  
     
     
         57 . The process of    claim 53   , wherein the feedstock Be comprises a single carbon cut composition.  
     
     
         58 . A composition comprising odd and even numbered olefins, said composition having an average carbon number ranging from C 5  to C 20 , comprising: 
 a) at least two linear alpha olefin species having different carbon chain lengths;    b) the two most predominant (on a mole basis) linear alpha olefin species of the at least two linear alpha olefin species are each within the range of C 5  to C 20 ;    
       c) said two most predominant linear alpha olefin species are present in an amount of at least 20 wt %, based on the weight of the olefins in the composition; 
 d) cumulatively, the total amount of linear alpha olefins present in the composition within said range, inclusive, is at least 40 wt. %, based on the weight of the olefins in the composition;  
 e) one or more odd numbered olefins within the range present in an amount of at least 10 wt. %, cumulative; and  
 f) a cumulative amount of aromatics, saturated hydrocarbons, and oxygenates of 5 wt. % or less, based on the weight of the composition.  
 
     
     
         59 . The composition of    claim 58   , wherein the amount of said two most predominately linear alpha olefins is at least 30 wt. %.  
     
     
         60 . The composition of    claim 58   , wherein the amount of odd numbered olefins is at least 20 wt. %, cumulative.  
     
     
         61 . The composition of    claim 58   , wherein one of said two most predominant linear alpha olefin species is an odd numbered linear alpha olefin.  
     
     
         62 . The composition of    claim 58   , wherein said total cumulative amount of linear alpha olefins is at least 70 wt. %.  
     
     
         63 . The composition of    claim 58   , wherein said total amount of aromatics, saturated hydrocarbons, and oxygenates is 2 wt. % or less.  
     
     
         64 . The composition of    claim 58   , wherein the carbon number range of the composition ranges from C 1  to C 18 .  
     
     
         65 . The composition of    claim 58   , wherein the two most predominant linear alpha olefin species are present in an amount of at least 30 wt. % based on the weight of the composition.  
     
     
         66 . The composition of    claim 58   , wherein the cumulative amount of linear alpha olefins is at least 70 wt. %, the amount of odd numbered olefins is at least 30 wt. %, and the cumulative amount of aromatics, saturated hydrocarbons, and oxygenates is 2 wt. % or less.  
     
     
         67 . The composition of    claim 58   , further comprising 6 wt. % or less of branched olefins having branching at the C 2  or C 3  position relative to the most proximate double bond.  
     
     
         68 . The composition of    claim 58   , further comprising 4 wt. % or less of branched olefins having branching at the C 2  or C 3  position relative to the most proximate double bond.  
     
     
         69 . The composition of    claim 58   , wherein the amount of odd numbered olefins is at least 30 wt. %, cumulative.  
     
     
         70 . A composition having an average carbon number ranging from C 6  to C 18  comprising at least two linear alpha olefin species having different carbon chain lengths within said range, inclusive, at least 50 wt. % of linear alpha olefins, where the composition has a most predominant olefin species represented by n carbon numbers, wherein the next most predominant olefin species has either n+1 or n−1 carbon numbers; wherein said composition comprises 2 wt. % or less of saturated hydrocarbons.  
     
     
         71 . The composition of claim  70 , further comprising branched olefins containing branching at the C 2  or C 3  positions, relative to the most proximate double bond, in an amount of 6 wt. %, based on the weight of the composition.  
     
     
         72 . The composition of claim  70 , further comprising branched olefins containing branching at the C 2  or C 3  positions, relative to the most proximate double bond, in an amount of 4 wt. %, based on the weight of the composition.  
     
     
         73 . The composition of claim  70 , wherein the composition comprises 1 wt. % or less of saturated hydrocarbons.  
     
     
         74 . The composition of claim  70 , comprising 4 wt. % or less branched olefins.  
     
     
         75 . The composition of claim  70 , comprising at least 70 wt. % linear alpha olefins.