Methods of preparing branched aliphatic alcohols

Abstract

Systems and methods to produced branched aliphatic alcohols are described. Systems may include a dehydrogenation-isomerization unit, an olefin dimerization unit, an olefin isomerization unit, a hydroformylation unit, a dehydrogenation unit, a hydrogenation unit and/or combinations thereof. Methods for producing branched aliphatic alcohols may include isomerization of olefins in a process stream. The isomerized olefins may be hydroformylated to produce aliphatic alcohols. After hydroformylation of the aliphatic alcohols, unreacted components from the hydroformylation process may be separated from the aliphatic alcohols products. The unreacted components from the hydroformylation process may be recycled back into the main process stream or sent to other processing units. Addition of multiple streams to the units may be performed to control reaction conditions in the units.

1 - 204 . (canceled)  
     
     
         205 . A method for the production of aliphatic alcohols, comprising: 
 introducing a first hydrocarbon stream comprising olefins and paraffins into an isomerization unit, wherein the isomerization unit is configured to isomerize at least a portion of linear olefins in the first hydrocarbon stream to branched olefins, and wherein at least a portion of the unreacted components of the first hydrocarbon stream and at least a portion of the produced branched olefins form a second hydrocarbon stream;    introducing at least a portion of the second hydrocarbon stream into a hydroformylation unit, wherein the hydroformylation unit is configured to hydroformylate at least a portion of the olefins in the second hydrocarbon stream to produce aliphatic alcohols, and wherein at least a portion of the produced aliphatic alcohols comprises a branched alkyl group, and wherein at least a portion of the unreacted components of the second hydrocarbon stream, and at least a portion of the produced aliphatic alcohols form a hydroformylation reaction stream;    separating at least a portion of the hydroformylation reaction stream to produce an aliphatic alcohol product stream and a paraffins and unreacted olefins stream; and    introducing at least a portion of the paraffins and unreacted olefins stream into a dehydrogenation unit, wherein the dehydrogenation unit is configured to dehydrogenate at least a portion of paraffins in the paraffins and unreacted olefins stream to produce olefins, and wherein at least a portion of the produced olefins exits the dehydrogenation unit to form an olefinic hydrocarbon stream; and    introducing at least a portion of the olefinic hydrocarbon stream into the isomerization unit.    
     
     
         206 . The method of  claim 205 , wherein the first hydrocarbon stream is produced from an olefin oligomerization process.  
     
     
         207 . The method of  claim 205 , wherein the first hydrocarbon stream is produced from a Fischer-Tropsch process.  
     
     
         208 . The method of  claim 205 , wherein the first hydrocarbon stream comprises olefins and paraffins having a carbon number from 10 to 13.  
     
     
         209 . The method of  claim 205 , wherein the first hydrocarbon stream comprises olefins and paraffins having a carbon number from 10 to 17.  
     
     
         210 . The method of  claim 205 , wherein the isomerization unit is operated at a reaction temperature between about 200° C. and about 500° C.  
     
     
         211 . The method of  claim 205 , wherein the isomerization unit is operated at a reaction pressure between about 0.1 atmosphere and about 20 atmospheres.  
     
     
         212 . The method of  claim 205 , wherein at least a portion of the branched olefins comprise an average number of branches per total olefin molecules of at least 0.7.  
     
     
         213 . The method of  claim 205 , wherein at least a portion of the branched olefins comprise methyl and ethyl branches.  
     
     
         214 . The method of  claim 205 , wherein at least a portion of the branched olefins comprise an average number of branches per total olefin molecules of less than 2.5.  
     
     
         215 . The method of  claim 205 , wherein at least a portion of the branched olefins comprise an average number of branches per total olefin molecules of between about 0.7 and about 2.2.  
     
     
         216 . The method of  claim 205 , wherein at least a portion of the branched olefins comprise an average number of branches per total olefin molecules of between about 1.0 and about 2.2.  
     
     
         217 . The method of  claim 205 , wherein greater than 50 percent of the branched groups on the branched olefins are methyl groups.  
     
     
         218 . The method of  claim 205 , wherein less than 30 percent of the branched groups on the branched olefins are ethyl groups.  
     
     
         219 . The method of  claim 205 , wherein less than 10 percent of the branched groups on the branched olefins are groups other than methyl or ethyl groups.  
     
     
         220 . The method of  claim 205 , wherein the branched olefins have less than 0.5 percent aliphatic quaternary carbon atoms.  
     
     
         221 . The method of  claim 205 , wherein the branched olefins have less than 0.3 percent aliphatic quaternary carbon atoms.  
     
     
         222 . The method of  claim 205 , wherein the hydroformylation unit is configured to produce greater than 50 percent of aliphatic alcohols.  
     
     
         223 . The method of  claim 205 , wherein the hydroformylation unit is configured to produce greater than 95 percent of aliphatic alcohols.  
     
     
         224 . The method of  claim 205 , wherein the hydroformylation unit is operated at a reaction temperature from about 100° C. to about 300° C.  
     
     
         225 . The method of  claim 205 , wherein the branched alkyl groups of the aliphatic alcohols comprise about 0.5 percent or less aliphatic quaternary carbon atoms, and an average number of branches per alkyl group of at least 0.7, the branches comprising methyl and ethyl branches.  
     
     
         226 . The method of  claim 205 , further comprising adjusting a ratio of olefins to paraffins introduced into the isomerization unit by adding at least a portion of a paraffinic hydrocarbon stream into the isomerization unit.  
     
     
         227 . The method of  claim 205 , further comprising: 
 adjusting a ratio of olefins to paraffins introduced into the isomerization unit by combining a paraffinic hydrocarbon stream with at least a portion of the first hydrocarbon stream upstream of the isomerization unit to form a combined stream; and    introducing the combined stream into the isomerization unit.    
     
     
         228 . The method of  claim 205 , further comprising adjusting a ratio of olefins to paraffins introduced into the hydroformylation unit by adding at least a portion of a third hydrocarbon stream into the hydroformylation unit.  
     
     
         229 . The method of  claim 205 , further comprising adjusting a ratio of olefins to paraffins introduced into the hydroformylation unit by adding at least a portion of a third hydrocarbon stream into the hydroformylation unit, wherein the third hydrocarbon stream comprises greater than 80 percent olefins by weight.  
     
     
         230 . The method of  claim 205 , further comprising: 
 adjusting a ratio of olefins to paraffins introduced into the hydroformylation unit by combining at least a portion of a third hydrocarbon stream with at least a portion of the second hydrocarbon stream upstream of the hydroformylation unit to form a combined stream; and    introducing the combined stream into the hydroformylation unit.    
     
     
         231 . The method of  claim 205 , further comprising: 
 adjusting a ratio of olefins to paraffins introduced into the hydroformylation unit by combining at least a portion of a third hydrocarbon stream with at least a portion of the second hydrocarbon stream upstream of the hydroformylation unit to form a combined stream, wherein the third hydrocarbon stream comprises greater than 80 percent olefins by weight; and    introducing the combined stream into the hydroformylation unit.    
     
     
         232 . The method of  claim 205 , further comprising: 
 adjusting a ratio of olefins to paraffins introduced into the hydroformylation unit by combining at least a portion of a third hydrocarbon stream with at least a portion of the second hydrocarbon stream upstream of the hydroformylation unit to form a combined stream, wherein the third hydrocarbon stream comprises linear olefins; and    introducing the combined stream into the hydroformylation unit.    
     
     
         233 . The method of claim  250 , further comprising: 
 adjusting a ratio of olefins to paraffins introduced into the hydroformylation unit by combining at least a portion of a third hydrocarbon stream with at least a portion of the second hydrocarbon stream upstream of the hydroformylation unit to form a combined stream, wherein at least a portion of the second hydrocarbon stream comprises branched olefins; and    introducing the combined stream into the hydroformylation unit.    
     
     
         234 . The method of  claim 205 , further comprising: 
 adjusting a ratio of olefins to paraffins introduced into the hydroformylation unit by combining at least a portion of a third hydrocarbon stream with at least a portion of the second hydrocarbon stream upstream of the hydroformylation unit to form a combined stream, wherein at least a portion of the third hydrocarbon stream comprises linear olefins and at least a portion of the second hydrocarbon stream comprises branched olefins; and    introducing the combined stream into the hydroformylation unit.    
     
     
         235 . The method of  claim 205 , further comprising: 
 adjusting a ratio of olefins to paraffins introduced into the isomerization unit by combining at least a portion of a paraffinic hydrocarbon stream with at least a portion of the first hydrocarbon stream upstream of the isomerization unit to form a combined stream;    introducing the combined stream into the isomerization unit;    adjusting a ratio of olefins to paraffins introduced into the hydroformylation unit by combining at least a portion of a third hydrocarbon stream with at least a portion of the second hydrocarbon stream upstream of the hydroformylation unit to form a combined stream; and    introducing the combined stream into the hydroformylation unit.    
     
     
         236 . The method of  claim 205 , wherein the dehydrogenation unit is operated at a temperature between about 300° C. and about 700° C.  
     
     
         237 . The method of  claim 205 , wherein the dehydrogenation unit is operated at a pressure between about 0.01 atmosphere and about 25 atmospheres.  
     
     
         238 . The method of  claim 205 , further comprising introducing at least a portion of the aliphatic alcohol product stream into a sulfation unit, wherein the sulfation unit is configured to sulfate at least a portion of the aliphatic alcohols in the aliphatic alcohol product stream to produce aliphatic sulfates, and wherein at least a portion of the aliphatic sulfates produced comprises branched aliphatic sulfates.  
     
     
         239 . The method of  claim 205 , further comprising introducing at least a portion of the aliphatic alcohol product stream into an oxyalkylation unit, wherein the oxyalkylation unit is configured to oxyalkylate at least a portion of the aliphatic alcohols in the aliphatic alcohol product stream to produce oxyalkyl alcohols, wherein at least a portion of the oxyalkyl alcohols produced comprises branched oxyalkyl alcohols.  
     
     
         240 - 270 . (canceled)