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US 8,722,953 B2Granted
Method for producing dienes by hydrodimerization
AssigneeEvonik Degussa GmbH
InventorsVolker Brehme, Manfred Neumann, Frank Bauer, Elke Fiebig-Bauer, Franz Rudolf Bauer, Johanna Elisabeth Bauer, Dirk Roettger
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Abstract
The invention relates to a process for preparing substituted or unsubstituted 1,7-diolefins by hydrodimerizing non-cyclic olefins having at least two conjugated double bonds in the presence of a reducing agent and of a catalyst, wherein the catalyst used is a metal-carbene complex.
Claims22
A process for preparing a substituted or unsubstituted 1,7-diolefin, comprising:
- hydrodimerizing a non-cyclic olefin having at least two conjugated double bonds in a presence of a reducing agent and a catalyst,
- wherein the reducing agent comprises at least one selected from the group consisting of formic acid and a formate, the reducing agent is metered in during a course of the hydrodimerizing of the non-cyclic olefin such that a ratio of the non-cyclic olefin to the reducing agent is from 1:1 to 10:1, and the catalyst comprises a metal-carbene complex which has a metal of group 8 to 10 of the Periodic Table and at least one carbene ligand of the structure 2
- where:
- R1, R2=—(CH2)n—B
- B=mono- or polycyclic aryl group having 6 to 14 carbon atoms or mono- or polycyclic heterocycle having 5 to 14 carbon atoms and heteroatoms, where this heterocycle has 1 to 3 heteroatoms selected from the group consisting of N, O and S,
- n=0-4 and
- R3 and R4=substituents selected from the group consisting of hydrogen, alkyl, heteroaryl, aryl, —CN, —COOH, —COO-alkyl, —COO-aryl, —OCO-alkyl, OCO-aryl, —OCOO-alkyl, OCOO-aryl, —CHO, —CO-alkyl, —CO-aryl, —NH2, —NH(alkyl), —N(alkyl)2, NH(aryl), —N(aryl)2, —F, —Cl, —Br, —I, —OH, —CF3, —NO2, -ferrocenyl, —SO3H, and —PO3H2, where the alkyl groups have 1 to 12 carbon atoms and the aryl groups 5 to 14 carbon atoms, and the substituents of R3 and R4 may also be part of a bridging aliphatic or aromatic ring,
- and the substituents of R1 and R2 are the same or different and are substituted or unsubstituted, and the substituents of R3 and R4 are the same or different and are substituted or unsubstituted.
5 more elements
Dependencies are inferred from the claim text.