3760-13-2

Usage

Type of Compound

Organic compound

Structure

Cyclic hydrocarbon with a cyclooctadiene ring

Substituents

Two methyl groups at the 1 and 6 positions

Applications

a. Organic synthesis
b. Building block for various chemicals
c. Found in some natural products
d. Studied for potential biological activities

Stability

Stable under normal conditions

Usage

Reagent in various chemical reactions in the laboratory

InChI:InChI=1/C10H16/c1-9-5-3-4-6-10(2)8-7-9/h5-6H,3-4,7-8H2,1-2H3/b9-5-,10-6-

Upstream product

• 78-79-5 isoprene 

Relevant academic research and scientific papers

Producing cyclic fuels from conjugated diene

A method for making a fuel includes reacting a conjugated diene or a mixture of conjugated dienes with a catalyst selected from the group consisting of a low valent iron catalyst stabilized with a pyridineimine ligand, an iron precatalyst coordinated to the pyridineimine ligand that is activated with a reducing agent, a low oxidation state Fe complex stabilized with a pyridineimine ligand and a coordinating ligand, and combinations thereof, thereby forming a substituted cyclooctadiene. The substituted cyclooctadiene is then hydrogenated, thereby forming cyclooctane fuel.

[4 + 4]-cycloaddition of isoprene for the production of high-performance bio-based jet fuel

Isoprene was efficiently converted to 1,6-dimethyl-1,5-cyclooctadiene (DMCOD) by selective [4 + 4]-cycloaddition with a catalyst formed by in situ reduction of [(MePI)FeCl(μ-Cl)]2 (MePI = [2-(2,6-(CH3)2-C6H3-NC(CH3))-C4H5N]). DMCOD was isolated in 92% yield, at the preparative scale, with a catalyst loading of 0.025 mol%, and a TON of 3680. Catalytic hydrogenation of DMCOD yielded 1,4-dimethylcyclooctane (DMCO). The cyclic structure and ring strain of DMCO afforded gravimetric and volumetric net heats of combustion 2.4 and 9.2% higher, respectively, than conventional jet fuel. In addition, the presence of methyl branches at two sites resulted in a-20 °C kinematic viscosity of 4.17 mm2 s-1, 48% lower than the maximum allowed value for conventional jet fuel. The ability to derive isoprene and related alcohols readily from abundant biomass sources, coupled with the highly efficient [Fe]-catalyzed [4 + 4]-cycloaddition described herein, suggests that this process holds great promise for the economical production of high-performance, bio-based jet fuel blendstocks.

METHOD FOR PRODUCING TRIMETHYLCYCLODODECATRIENE

The invention relates to the production of trimethylcyclododecatriene in a continuous or discontinuous method, by the trimerisation of isoprene in the presence of a catalyst system and a solvent. The raw trimethylcyclododecatriene obtained can be isolated by distillation. The dimethylcyclooctadiene formed as a by-product can also be isolated from the raw product.