A synthesis method and a synthesis device of cyclododecene according to the present invention have a high conversion rate of cyclododecatriene which is a reactant and a high selectivity of cyclododecene which is a required product, and even so, have an effect of significantly decreasing a reaction time. In addition, the method and the device have an excellent conversion rate of cyclododecatriene and an excellent selectivity of cyclododecene, while maintaining excellent reactivity without an organic solvent such as ethanol. Therefore, a volume of the reactor relative to an output of cyclododecene may be further decreased. Moreover, the method and the device may minimize costs for facilities and process, are practical, decrease a process time, and are industrially advantageous for mass production as compared with the conventional art.

A synthesis method and a synthesis device of cyclododecene according to the present invention have a high conversion rate of cyclododecatriene which is a reactant and a high selectivity of cyclododecene which is a required product, and even so, have an effect of significantly decreasing a reaction time. In addition, the method and the device have an excellent conversion rate of cyclododecatriene and an excellent selectivity of cyclododecene, while maintaining excellent reactivity without an organic solvent such as ethanol. Therefore, a volume of the reactor relative to an output of cyclododecene may be further decreased. Moreover, the method and the device may minimize costs for facilities and process, are practical, decrease a process time, and are industrially advantageous for mass production as compared with the conventional art.

Provided is a method for preparing 1-butene and propylene including: supplying a C4 mixture stream to a first hydrogenation reactor to convert 1,3-butadiene into 1-butene; supplying a discharge stream from the first hydrogenation reactor to a first distillation column, supplying a lower discharge stream from the first distillation column including 2-butene and n-butane to a metathesis reactor, and supplying an upper discharge stream from the first distillation column including 1-butene and i-butane to a second distillation column; recovering an upper discharge stream the second distillation column including i-butane and recovering 1-butene from a lower discharge stream from the second distillation column; and producing propylene in the metathesis reactor, supplying a discharge stream from the metathesis reactor to a purification unit to recover propylene, and recycling an unreacted material to the metathesis reactor.

Provided is a method for preparing 1-butene and propylene including: supplying a C4 mixture stream to a first hydrogenation reactor to convert 1,3-butadiene into 1-butene; supplying a discharge stream from the first hydrogenation reactor to a first distillation column, supplying a lower discharge stream from the first distillation column including 2-butene and n-butane to a metathesis reactor, and supplying an upper discharge stream from the first distillation column including 1-butene and i-butane to a second distillation column; recovering an upper discharge stream the second distillation column including i-butane and recovering 1-butene from a lower discharge stream from the second distillation column; and producing propylene in the metathesis reactor, supplying a discharge stream from the metathesis reactor to a purification unit to recover propylene, and recycling an unreacted material to the metathesis reactor.

A method of producing a fuel additive includes passing a feed stream comprising C4 hydrocarbons through a hydrogenation unit producing a hydrogenated stream; passing the hydrogenated stream through a distillation unit producing a first stream and a second stream; producing an isobutylene stream by passing the first stream through a molecular sieve unit; passing the isobutylene stream to a hydration unit as a feedstock for the fuel additive; and forming the fuel additive in the hydration unit.

A method of producing a fuel additive includes passing a feed stream comprising C4 hydrocarbons through a hydrogenation unit producing a hydrogenated stream; passing the hydrogenated stream through a distillation unit producing a first stream and a second stream; producing an isobutylene stream by passing the first stream through a molecular sieve unit; passing the isobutylene stream to a hydration unit as a feedstock for the fuel additive; and forming the fuel additive in the hydration unit.

A method of producing a fuel additive includes passing a feed stream comprising C4 hydrocarbons through a hydrogenation unit producing a hydrogenated stream; passing the hydrogenated stream through a distillation unit producing a first stream and a second stream; producing an isobutylene stream by passing the first stream through a molecular sieve unit; passing the isobutylene stream to a hydration unit as a feedstock for the fuel additive; and forming the fuel additive in the hydration unit.

The present invention pertains to a method for recovering a selective homogeneous hydrogenation catalyst and a method for reusing the recovered selective homogeneous hydrogenation catalyst. The method for recovering a selective homogeneous hydrogenation catalyst comprises: a step for synthesizing cyclododecene by selectively hydrogenating a first reaction solution containing cyclododecatriene, triphenylphosphine, formaldehyde, and ruthenium chloride, wherein a selective homogeneous hydrogenation catalyst is prepared during the selective hydrogenation reaction from the triphenylphosphine, formaldehyde, and ruthenium chloride to synthesize the cyclododecene; and a step for distilling and separating unreacted cyclododecatriene and cyclododecadiene, as well as the product cyclododecene, from a second reaction solution in which the cyclododecene synthesis has been completed, and recovering the selective homogeneous hydrogenation catalyst.

The present invention pertains to a method for recovering a selective homogeneous hydrogenation catalyst and a method for reusing the recovered selective homogeneous hydrogenation catalyst. The method for recovering a selective homogeneous hydrogenation catalyst comprises: a step for synthesizing cyclododecene by selectively hydrogenating a first reaction solution containing cyclododecatriene, triphenylphosphine, formaldehyde, and ruthenium chloride, wherein a selective homogeneous hydrogenation catalyst is prepared during the selective hydrogenation reaction from the triphenylphosphine, formaldehyde, and ruthenium chloride to synthesize the cyclododecene; and a step for distilling and separating unreacted cyclododecatriene and cyclododecadiene, as well as the product cyclododecene, from a second reaction solution in which the cyclododecene synthesis has been completed, and recovering the selective homogeneous hydrogenation catalyst.

The present invention pertains to a method for recovering a selective homogeneous hydrogenation catalyst and a method for reusing the recovered selective homogeneous hydrogenation catalyst. The method for recovering a selective homogeneous hydrogenation catalyst comprises: a step for synthesizing cyclododecene by selectively hydrogenating a first reaction solution containing cyclododecatriene, triphenylphosphine, formaldehyde, and ruthenium chloride, wherein a selective homogeneous hydrogenation catalyst is prepared during the selective hydrogenation reaction from the triphenylphosphine, formaldehyde, and ruthenium chloride to synthesize the cyclododecene; and a step for distilling and separating unreacted cyclododecatriene and cyclododecadiene, as well as the product cyclododecene, from a second reaction solution in which the cyclododecene synthesis has been completed, and recovering the selective homogeneous hydrogenation catalyst.