(Z)-pent-2-ene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a first reactor R1, 1-butene, 2-butene and isobutene are reacted in the presence of the metathesis catalyst of the present invention to give propene, 2-pentene and 2-methyl-2-butene. For this purpose, a raffinate I stream is fed to the reactor. The reactor is followed by a distillation column D1 at the top of which propene and ethene formed as by-product are removed. Unreacted raffinate I is taken off at the middle offtake. Some of it may: also be returned to the reactor R1 (not shown in FIG. 1). 2-Pentene, 2-methyl-2-butene and 3-hexene formed as by-product as well as high boilers are taken off at the bottom of D1. The bottoms are then fed together with added ethene to a reactor R2 which again contains a metathesis catalyst of the present invention. In this reactor R2, the reaction of 2-pentene and 2-methyl-2-butene with ethene to give 1-butene, isobutene and propene takes place. The reaction product from reactor R2 is fed to a distillation column D2 at the top of which propene and unreacted ethene are taken off. 1-Butene and isobutene formed are taken off at the middle offtake and at least sore is preferably returned to the reactor R1. Unreacted 2-pentene, 2-methyl-2-butene and also, as by-products, 3-hexene and high boilers are obtained at the bottom of D2. These are preferably returned to the reactor R2. The mixtures of propene and by-product ethene taken off at the top of D1 and D2 are fractionated in a further distillation column D3. Ethene is obtained at the top of D3 and this is preferably returned to the reactor R2 (not shown in FIG. 1), or discharged as co-cracker feed. The propene obtained at the bottom of D3 is the desired reaction product of the process of the present invention. D1 and D2 are designed such that a low-boiling phase, in particular a C2/3 phase comprising ethene and propene, is taken off at the top of the column. C4 streams, in particular butenes and butanes, are taken off as intermediate-boiling phase. As bottoms, C≧5-hydrocarbons are discharged.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a first reactor R1, 1-butene, 2-butene and isobutene are reacted in the presence of the metathesis catalyst of the present invention to give propene, 2-pentene and 2-methyl-2-butene. For this purpose, a raffinate I stream is fed to the reactor. The reactor is followed by a distillation column D1 at the top of which propene and ethene formed as by-product are removed. Unreacted raffinate I is taken off at the middle offtake. Some of it may: also be returned to the reactor R1 (not shown in FIG. 1). 2-Pentene, 2-methyl-2-butene and 3-hexene formed as by-product as well as high boilers are taken off at the bottom of D1. The bottoms are then fed together with added ethene to a reactor R2 which again contains a metathesis catalyst of the present invention. In this reactor R2, the reaction of 2-pentene and 2-methyl-2-butene with ethene to give 1-butene, isobutene and propene takes place. The reaction product from reactor R2 is fed to a distillation column D2 at the top of which propene and unreacted ethene are taken off. 1-Butene and isobutene formed are taken off at the middle offtake and at least sore is preferably returned to the reactor R1. Unreacted 2-pentene, 2-methyl-2-butene and also, as by-products, 3-hexene and high boilers are obtained at the bottom of D2. These are preferably returned to the reactor R2. The mixtures of propene and by-product ethene taken off at the top of D1 and D2 are fractionated in a further distillation column D3. Ethene is obtained at the top of D3 and this is preferably returned to the reactor R2 (not shown in FIG. 1), or discharged as co-cracker feed. The propene obtained at the bottom of D3 is the desired reaction product of the process of the present invention. D1 and D2 are designed such that a low-boiling phase, in particular a C2/3 phase comprising ethene and propene, is taken off at the top of the column. C4 streams, in particular butenes and butanes, are taken off as intermediate-boiling phase. As bottoms, C≧5-hydrocarbons are discharged.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a first reactor R1, 1-butene, 2-butene and isobutene are reacted in the presence of the metathesis catalyst of the present invention to give propene, 2-pentene and 2-methyl-2-butene. For this purpose, a raffinate I stream is fed to the reactor. The reactor is followed by a distillation column D1 at the top of which propene and ethene formed as by-product are removed. Unreacted raffinate I is taken off at the middle offtake. Some of it may: also be returned to the reactor R1 (not shown in FIG. 1). 2-Pentene, 2-methyl-2-butene and 3-hexene formed as by-product as well as high boilers are taken off at the bottom of D1. The bottoms are then fed together with added ethene to a reactor R2 which again contains a metathesis catalyst of the present invention. In this reactor R2, the reaction of 2-pentene and 2-methyl-2-butene with ethene to give 1-butene, isobutene and propene takes place. The reaction product from reactor R2 is fed to a distillation column D2 at the top of which propene and unreacted ethene are taken off. 1-Butene and isobutene formed are taken off at the middle offtake and at least sore is preferably returned to the reactor R1. Unreacted 2-pentene, 2-methyl-2-butene and also, as by-products, 3-hexene and high boilers are obtained at the bottom of D2. These are preferably returned to the reactor R2. The mixtures of propene and by-product ethene taken off at the top of D1 and D2 are fractionated in a further distillation column D3. Ethene is obtained at the top of D3 and this is preferably returned to the reactor R2 (not shown in FIG. 1), or discharged as co-cracker feed. The propene obtained at the bottom of D3 is the desired reaction product of the process of the present invention. D1 and D2 are designed such that a low-boiling phase, in particular a C2/3 phase comprising ethene and propene, is taken off at the top of the column. C4 streams, in particular butenes and butanes, are taken off as intermediate-boiling phase. As bottoms, C≧5-hydrocarbons are discharged.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Pentene from the raffinate II metathesis was dimerized continuously as in example 2 over an Ni heterogeneous catalyst. Fractional distillation of the product gave a decene fraction with a purity of 99.5%. Fractional distillation of the product

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 7a (9.47 g, 29.7 mmol, 1 equiv) in anhydrous THF at −78° C. under N2 was added a 1 M solution of LiHMDS in THF (33 mmol, 33 mL, 1.1 equiv) followed by cis-1-bromo-2-pentene (4.21 mL, 35.6 mmol, 1.2 equiv), afforded a mixture of diastereomers of the lactam 7b (R9′=2-pentene) (43.2%) after silica gel purification. The lactam 7b (3.96 g, 10.22 mmol) was reduced to the pyrrolidine 7c (R9′=2-pentene) by the two-step sequence involving superhydride® reduction of the lactam to the hemiaminal, at −78° C. in anhydrous THF, and the subsequent reduction of the hemiaminal with Et3SiH/BF3OEt2 in anhydrous DCM at −78° C., affording 7c (R9′=2-pentene) (71%) after silica gel purification. The pyrrolidine 7c (2.71 g, 7.26 mmol) and 10% palladium on carbon (560 mg) in anhydrous methanol (30 mL) was subjected to Parr hydrogenolysis at 50 psi for 5 h. The reaction mixture was filtered through a celite pad and washed several times with methanol. The combined washings and filtrate were evaporated to dryness, affording, without further purification, a colorless oil 7d (R9=pentyl) (1.68 g, 80%); TLC: Rf=0.3 [Solvent system: DCM:hexanes:MeOH (6:5:1)]. MS (ESNEG): 284.5 [M−H]−. afforded after silica gel purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a first reactor R1, 1-butene, 2-butene and isobutene are reacted in the presence of the metathesis catalyst of the present invention to give propene, 2-pentene and 2-methyl-2-butene. For this purpose, a raffinate I stream is fed to the reactor. The reactor is followed by a distillation column D1 at the top of which propene and ethene formed as by-product are removed. Unreacted raffinate I is taken off at the middle offtake. Some of it may: also be returned to the reactor R1 (not shown in FIG. 1). 2-Pentene, 2-methyl-2-butene and 3-hexene formed as by-product as well as high boilers are taken off at the bottom of D1. The bottoms are then fed together with added ethene to a reactor R2 which again contains a metathesis catalyst of the present invention. In this reactor R2, the reaction of 2-pentene and 2-methyl-2-butene with ethene to give 1-butene, isobutene and propene takes place. The reaction product from reactor R2 is fed to a distillation column D2 at the top of which propene and unreacted ethene are taken off. 1-Butene and isobutene formed are taken off at the middle offtake and at least sore is preferably returned to the reactor R1. Unreacted 2-pentene, 2-methyl-2-butene and also, as by-products, 3-hexene and high boilers are obtained at the bottom of D2. These are preferably returned to the reactor R2. The mixtures of propene and by-product ethene taken off at the top of D1 and D2 are fractionated in a further distillation column D3. Ethene is obtained at the top of D3 and this is preferably returned to the reactor R2 (not shown in FIG. 1), or discharged as co-cracker feed. The propene obtained at the bottom of D3 is the desired reaction product of the process of the present invention. D1 and D2 are designed such that a low-boiling phase, in particular a C2/3 phase comprising ethene and propene, is taken off at the top of the column. C4 streams, in particular butenes and butanes, are taken off as intermediate-boiling phase. As bottoms, C≧5-hydrocarbons are discharged.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a first reactor R1, 1-butene, 2-butene and isobutene are reacted in the presence of the metathesis catalyst of the present invention to give propene, 2-pentene and 2-methyl-2-butene. For this purpose, a raffinate I stream is fed to the reactor. The reactor is followed by a distillation column D1 at the top of which propene and ethene formed as by-product are removed. Unreacted raffinate I is taken off at the middle offtake. Some of it may: also be returned to the reactor R1 (not shown in FIG. 1). 2-Pentene, 2-methyl-2-butene and 3-hexene formed as by-product as well as high boilers are taken off at the bottom of D1. The bottoms are then fed together with added ethene to a reactor R2 which again contains a metathesis catalyst of the present invention. In this reactor R2, the reaction of 2-pentene and 2-methyl-2-butene with ethene to give 1-butene, isobutene and propene takes place. The reaction product from reactor R2 is fed to a distillation column D2 at the top of which propene and unreacted ethene are taken off. 1-Butene and isobutene formed are taken off at the middle offtake and at least sore is preferably returned to the reactor R1. Unreacted 2-pentene, 2-methyl-2-butene and also, as by-products, 3-hexene and high boilers are obtained at the bottom of D2. These are preferably returned to the reactor R2. The mixtures of propene and by-product ethene taken off at the top of D1 and D2 are fractionated in a further distillation column D3. Ethene is obtained at the top of D3 and this is preferably returned to the reactor R2 (not shown in FIG. 1), or discharged as co-cracker feed. The propene obtained at the bottom of D3 is the desired reaction product of the process of the present invention. D1 and D2 are designed such that a low-boiling phase, in particular a C2/3 phase comprising ethene and propene, is taken off at the top of the column. C4 streams, in particular butenes and butanes, are taken off as intermediate-boiling phase. As bottoms, C≧5-hydrocarbons are discharged.