3710-41-6

Usage

Physical state

Colorless liquid

Odor

Strong, unpleasant

Flammability

Highly flammable

Main use

Monomer in the production of synthetic rubber

Specific application

Synthesis of polyoctenamer

Additional use

Crosslinking agent in the production of resins and polymers

Potential applications

Organic synthesis and as a solvent in certain chemical processes

Toxicity

Toxic if ingested

Hazards

Can cause skin and eye irritation upon contact

Safety precautions

Handle with care

InChI:InChI=1/C8H14/c1-3-5-7-8-6-4-2/h3-4,6H,1,5,7-8H2,2H3/b6-4+

Upstream product

• 15972-89-1 (E)-1-phenoxy-2,7-octadiene 
• 15972-91-5 3-Phenoxy-1,7-octadien 
• 30460-73-2 (E)-1-acetoxy-2,7-octadiene 
• 106-99-0 buta-1,3-diene 
• 39252-64-7 2,7-octadienyl formate 
• 64-18-6 formic acid 
• 92747-31-4 (E)-2,7-octadienyl methyl carbonate 
• 3491-26-7 octa-1,7-dien-3-yl acetate 

Relevant academic research and scientific papers

METHOD FOR PRODUCING OCTADIENE

An object of the present invention is to provide a process for producing an octadiene from 2,7-octadienyl formate in an industrially useful manner in which palladium can maintain its catalytic activity for a long period of time. More specifically, the present invention relates to a process for producing an octadiene which includes the steps of continuously adding 2,7-octadienyl formate into a reaction system in which a mixture of a palladium compound, a tertiary organophosphorus compound and a solvent is present; and subjecting the 2,7-octadienyl formate to reaction while continuously distilling off a reaction product containing the resulting octadiene out of the reaction system.

METHOD FOR PRODUCING DIENES BY HYDRODIMERIZATION

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.

PROCESS FOR PRODUCING 1-OCTENE FROM BUTADIENE IN THE PRESENCE OF TITANIUM CATALYSTS

A method is described for the preparation of 1-octene starting from butadiene, wherein in a first step (a) the bis-hydrodimerization of butadiene to 1,7-octadiene is effected in the presence of a catalyst based on palladium containing one or more tri-substituted monodentate phosphines, in an aprotic polar solvent, in a second step (b) the partial catalytic hydrogenation of 1,7-octadiene to 1-octene is effected in the presence of a titanium compound activated with one or more metal alkyls of group 13 (selected from boron, aluminum, gallium, indium).

PROCESS FOR THE PREPARATION OF 1-OCTENE

Process in two steps for the preparation of 1-octene starting from butadiene which comprises: a first step (a) in which the bis-hydrodimerization of butadiene to 1,7-octadiene is effected in the presence of a catalyst based on a palladium complex containing one or more tri-substituted monodentate phosphines, in an aprotic polar solvent optionally containing an organic base; a second step (b) in which the partial catalytic hydrogenation of 1,7-octadiene to 1-octene is effected, the above process being characterized in that: (i) in the first step the aprotic polar solvent is selected from disubstituted cyclic ureas; (ii) in the second step the catalyst is selected from non- supported ruthenium complexes having general formula (I I): RuXmLn (I I).

Synthesis and Properties of (η3-1-Methylallyl)palladium(II) Formates as Models of Intermediates in the Palladium-Catalyzed Reductive Cleavage of Allylic Carboxylates and Carbonates with Formic Acid

In order to gain insight into the mechanism of the regioselective formation of alkenes in the palladium-catalyzed reductive cleavage of allylic carboxylates or carbonates with formic acid, two types of (η3-1-methylallyl)palladium formates (P1 and P2 types) have been prepared as simple models of catalytic intermediates. The P1 type is a neutral complex coordinated with one tertiary phosphine ligand and a formato ligand: [Pd(η3-MeCHCHCH2)(O2CH)(L)] (L = PMePh2, PMe2Ph, PMe3, P(o-tolyl)3); the P2 type is a cationic complex bearing two tertiary phosphine ligands and a formate counter anion: [Pd(η3-MeCHCHCH2)L2]+CO2H- (L = PMePh2, PMe2Ph, PMe3). The structures and dynamic behavior of the complexes in solution have been examined in detail by NMR spectroscopy. Studies on the thermolysis of the P1 and P2-type complexes have clearly provided the following mechanistic viewpoints: (1) 1-butene and 2-butene are formed from the P1 species; (2) butadiene is liberated from the P2 species; (3) the ratio of 1-butene to 2-butene increases as the bulkiness of phosphine ligand increases. A mechanism involving two geometrical isomers of [Pd(η3-MeCHCHCH2)(H)(L)], which are formed by decarboxylation of the P1-type complexes, has been proposed for the formation of butenes.

Preparation of 1-Alkenes by the Palladium-Catalyzed Hydrogenolysis of Terminal Allylic Carbonates and Acetates with Formic Acid-Triethylamine

A useful method for the preparation of 1-alkenes from terminal allylic carbonates and acetates by the palladium-catalyzed reaction with formates is described.Formic acid-triethylamine is a suitable reductant.As catalyst, Pd2(dba)3CHCl3-P(n-Bu)3 gave the best result, 0.05-0.2 molpercent being sufficient (turnover 500-2000).Using this method, various 1-alkenes were prepared in good yields with high selectivity.

REGIOSELECTIVE SYNTHESIS OF 1-OLEFINS BY PALLADIUM-CATALYZED HYDROGENOLYSIS OF TERMINAL ALLYLIC COMPOUNDS WITH AMMONIUM FORMATE

Various terminal allylic compounds such as allylic esters, phenyl esters, carbonates, chlorides, and vinyl epoxides react with ammonium or sodium formate to give 1-olefins with high regioselectivity by using palladium-tributylphosphine complex as a catalyst.The reaction offers a useful synthetic method for 1-olefins.