Fuel compositions comprising isoprene derivatives

Abstract

The invention provides for methods, compositions and systems using bioisoprene derived from renewable carbon for production of a variety of hydrocarbon fuels and fuel additives.

1 . A method for producing a fuel constituent from a bioisoprene composition comprising chemically transforming a substantial portion of the isoprene in the bioisoprene composition to non-isoprene compounds by:
 (a) subjecting the bioisoprene composition to heat or catalytic conditions suitable for isoprene dimerization to produce an isoprene dimer and then catalytically hydrogenating the isoprene dimer to form a saturated C10 fuel constituent; or   (b) (i) partially hydrogenating the bioisoprene composition to produce an isoamylene, (ii) dimerizing the isoamylene with a mono-olefin selected from the group consisting of isoamylene, propylene and isobutene to form a dimate and (iii) completely hydrogenating the dimate to produce a fuel constituent.   
     
     
         2 . The method of  claim 1 , wherein at least about 95% of isoprene in the bioisoprene composition is converted to non-isoprene compounds. 
     
     
         3 . The method of  claim 1 , wherein the bioisoprene composition is heated to about 150° C. to about 250° C. to produce an unsaturated cyclic isoprene dimer and the unsaturated cyclic isoprene dimer is hydrogenated catalytically to produce a saturated cyclic isoprene dimer fuel constituent. 
     
     
         4 . The method of  claim 1 , wherein the method comprises: (i) contacting the bioisoprene composition with a catalyst for catalyzing cyclo-dimerization of isoprene to produce an unsaturated cyclic isoprene dimer and the unsaturated cyclic isoprene dimer is hydrogenated catalytically to produce a saturated cyclic isoprene dimer fuel constituent. 
     
     
         5 . The method of  claim 4 , wherein the catalyst for catalyzing cyclo-dimerization of isoprene comprising a catalyst selected from the group consisting of a nickel catalyst, iron catalysts and chromium catalysts. 
     
     
         6 . The method of  claim 1 , wherein the step of partially hydrogenating the bioisoprene composition comprises contacting the bioisoprene composition with hydrogen gas and a catalyst for catalyzing partial hydrogenation of isoprene. 
     
     
         7 . The method of  claim 6 , wherein the catalyst for catalyzing partial hydrogenation of isoprene comprises a palladium catalyst. 
     
     
         8 . The method of  claim 1 , wherein the step of dimerizing the isoamylene with a mono-olefin comprises contacting the isoamylene with the mono-olefin in the presence of a catalyst for catalyzing dimerization of mono-olefin. 
     
     
         9 . The method of  claim 8 , wherein the catalyst for catalyzing dimerization of mono-olefin comprises an acid catalyst. 
     
     
         10 . The method of  claim 1 , further comprising purifying the isoprene from the bioisoprene composition prior to chemically transforming the bioisoprene composition to a fuel constituent. 
     
     
         11 . A system for producing a fuel constituent from a bioisoprene composition, wherein a substantial portion of the isoprene in the bioisoprene composition is chemically converted to non-isoprene compounds, the system comprising a bioisoprene composition and:
 (a) (i) one or more chemicals capable of dimerizing isoprene in the bioisoprene composition or a source of heat capable of dimerizing isoprene in the bioisoprene composition; and (ii) a catalyst capable of hydrogenating the isoprene dimer to form a saturated C10 fuel constituent; or   (b) (i) a chemical capable of partially hydrogenating isoprene in the bioisoprene composition to produce an isoamylene, (ii) a chemical capable of dimerizing the isoamylene with mono-olefins selected from the group consisting of isoamylene, propylene and isobutene to form a dimate and (iii) a chemical capable of completely hydrogenating the dimate to produce a fuel constituent.   
     
     
         12 . The system of  claim 11 , wherein the bioisoprene composition comprising greater than about 2 mg of isoprene and comprising greater than or about 99.94% isoprene by weight compared to the total weight of all C5 hydrocarbons in the composition. 
     
     
         13 . The system of  claim 11 , wherein the one or more chemicals capable of dimerizing isoprene comprises catalyst for catalyzing cyclo-dimerization of isoprene comprising a catalyst selected from the group consisting of ruthenium catalysts, nickel catalysts, iron catalysts and chromium catalysts. 
     
     
         14 . The system of  claim 11 , wherein the catalyst for hydrogenating the unsaturated isoprene dimers comprises a catalyst selected from the group consisting of palladium catalysts, nickel catalysts, ruthenium catalysts and rhodium catalysts. 
     
     
         15 . The system of  claim 11 , wherein the chemical capable of partially hydrogenating isoprene comprises a palladium catalyst. 
     
     
         16 . The system of  claim 11 , wherein the chemical capable of dimerizing the isoamylene with mono-olefins comprises an acid catalyst. 
     
     
         17 . A fuel composition comprising a fuel constituent produced by the method of  claim 1 . 
     
     
         18 . The fuel composition of  claim 17 , wherein the fuel composition is substantially free of isoprene. 
     
     
         19 . The fuel composition of  claim 17 , wherein the fuel composition has δ 13 C value which is greater than −22‰ or within the range of −32‰ to −24‰.