7206-25-9

Usage

Uses

Used in Chemical Industry:
(E)-9-Octadecene is used as a solvent for various chemical processes due to its ability to dissolve a wide array of substances, facilitating smoother and more efficient reactions.
Used in Lubricant Production:
(E)-9-Octadecene is used as a lubricant in the manufacturing of machinery components, as its low volatility and high boiling point contribute to its effectiveness in reducing friction and wear.
Used in Plastics and Waxes Production:
(E)-9-Octadecene is used as a precursor in the synthesis of plastics, waxes, and other polymers, providing a foundation for the creation of durable and versatile materials.
Used in Cosmetics Industry:
(E)-9-Octadecene is used as an ingredient in the cosmetics industry, where its unique properties contribute to the formulation of various products, enhancing their performance and quality.
Used in Surfactant and Emulsifier Production:
(E)-9-Octadecene is used as a key component in the manufacture of surfactants and emulsifiers, which are essential in stabilizing mixtures and creating consistent products across various industries.
Used in Specialty Chemicals:
(E)-9-Octadecene is utilized in the production of specialty chemicals, where its unique chemical properties make it a valuable and versatile ingredient for a multitude of applications.

Upstream product

• 112-62-9 octadec-9-enoic acid methyl ester 
• 112-62-9 Methyl oleate 
• 74-85-1 ethene 
• 87057-47-4 2,3-Dioctyl-thiirane 
• 872-05-9 1-Decene 
• 108-88-3 toluene 
• 107-13-1 acrylonitrile 
• 2462-84-2 methyl (9E)-octadec-9-enoate 
• 41446-62-2 (Z)-5-tetradecene 
• 25260-60-0 cis-1,4-bis(acetyloxy)but-2-ene 
• 645-49-8 cis-stilben 
• 7642-15-1 (Z)-oct-4-ene 
• 1080-12-2 Dehydrozingerone 
• 762-72-1 allyl-trimethyl-silane 

Downstream Products

• 1454-84-8 nonadecan-1-ol 
• 69814-33-1 (9R,10S)-10-Phenylselanyl-octadecan-9-ol 
• 6583-67-1 2-Phenyl-octadecan 
• 13419-26-6 5-Phenyl-octadecan 
• 13419-25-5 4-Phenyl-octadecan 
• 13419-24-4 3-Phenyl-octadecan 
• 872-05-9 1-Decene 
• 74-85-1 ethene 
• 17527-28-5 1,2-Dicyclohexenylethylen 
• 83026-58-8 ((Z)-4-Dec-1-enyl)-cyclohexene 
• 143-08-8 nonyl alcohol 
• 112-05-0 nonanoic acid 
• 1577-43-1 nonadecyl acetate 

Relevant academic research and scientific papers

Supported Ru olefin metathesis catalysts: Via a thiolate tether

Thiolate-coordinated ruthenium alkylidene complexes can give high Z-selectivity and stereoretentivity in olefin metathesis. To investigate their applicability as heterogeneous catalysts, we have successfully developed a methodology to easily immobilize prototype ruthenium alkylidenes onto hybrid mesostructured silica via a thiolate tether. In contrast, the preparation of the corresponding molecular complexes appeared very challenging in solution. These prototype supported complexes contain small thiolates but still, they are slightly more Z-selective than their molecular analogues. These results open the door to more active and selective heterogeneous catalysts by supporting more advanced thiolate Ru-complexes.

USE OF RUTHENIUM COMPLEXES IN OLEFIN METATHESIS REACTION

The invention relates to the use of ruthenium complexes, which are homogeneous catalysts and/or precatalysts of the olefin metathesis reaction, which lead to the production of alkenes containing an internal (non-terminal) double C=C bond.

SYNTHESIS AND CHARACTERIZATION OF METATHESIS CATALYSTS

This invention relates generally to olefin metathesis catalysts, to the preparation of such compounds, compositions comprising such compounds, methods of using such compounds, and the use of such compounds in the metathesis of olefins and in the synthesis of related olefin metathesis catalysts. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and in industrial applications such as oil and gas, fine chemicals, and pharmaceuticals.

Synthesis and Catalytic Properties of Sulfur-Chelated Ruthenium Benzylidenes Bearing a Cyclic (Alkyl)(amino)carbene Ligand

Sulfur-chelated ruthenium olefin metathesis precatalysts that possess cyclic (alkyl)(amino)carbenes (CAAC) can benefit from the synergetic effect of both ligands. Changing the steric bulk of the CAAC ligand by using different substitution patterns was shown to affect the geometry of the complexes produced and determined whether the complexes could be catalytically dormant. The cis-dichloro latent catalysts could be activated both by heat or light, even in the visible region, for representative acyclic diene metathesis and ring-opening metathesis polymerization reactions, olefin cross-metathesis, and ring-closing metathesis without isomerization byproducts. Thus, these complexes were shown to combine the uniqueness of CAAC-containing Ru olefin metathesis catalysts with the advantage of the thermal and photolatency imposed by sulfur chelation of the benzylidene.

Stereoretentive Olefin Metathesis Made Easy: In Situ Generation of Highly Selective Ruthenium Catalysts from Commercial Starting Materials

The in situ preparation of highly stereoretentive ruthenium-based metathesis catalysts is reported. This approach completely avoids the isolation of intermediates and air-sensitive catalysts, thus allowing for the rapid access and evaluation of numerous dithiolate Ru catalysts. A procedure was established to perform cross-metathesis reactions without the use of a glovebox, and on a small scale even Schlenk techniques are not required. Consequently, the chemistry displayed in this report is available to every practicing organic chemist and presents a powerful approach for the identification of new stereoretentive catalysts.

Synthesis and Evaluation of Sterically Demanding Ruthenium Dithiolate Catalysts for Stereoretentive Olefin Metathesis

Dithiolate ligands have recently been used in ruthenium-catalyzed olefin metathesis and have provided access to a kinetically E selective pathway through stereoretentive olefin metathesis. The typical dithiolate used is relatively simple with low steric demands imparted on the catalyst. We have developed a synthetic route that allows access to sterically demanding dithiolate ligands. The catalysts generated provided a pathway to study the intricate structure-activity relationships in olefin metathesis. It was found that DFT calculations can predict the ligand arrangement around the ruthenium center with remarkable accuracy. These dithiolate catalysts proved resistant to ligand isomerization and were stable even under forcing conditions. Additionally, catalyst initiation and olefin metathesis studies delivered a better understanding to the interplay between dithiolate ligand structure and catalyst activity and selectivity.

Fast-initiating, ruthenium-based catalysts for improved activity in highly E-selective cross metathesis

Ruthenium-based olefin metathesis catalysts bearing dithiolate ligands have been recently employed to generate olefins with high E-selectivity (>99% E) but have been limited by low to moderate yields. In this report, 1H NMR studies reveal that a major contributing factor to this low activity is the extremely low initiation rates of these catalysts with trans olefins. Introducing a 2-isopropoxy-3-phenylbenzylidene ligand in place of the conventional 2-isopropoxybenzylidene ligand resulted in catalysts that initiate rapidly under reaction conditions. As a result, reactions were completed in significantly less time and delivered higher yields than those in previous reports while maintaining high stereoselectivity (>99% E).

OLEFIN METATHESIS CATALYSTS

This invention relates generally to metathesis catalysts and the use of such catalysts in the metathesis of olefins and olefin compounds, more particularly, in the use of such catalysts in Z and E selective olefin metathesis reactions. The invention has utility in the fields of organometallics and organic synthesis.

Cross metathesis of methyl oleate (MO) with terminal, internal olefins by ruthenium catalysts: Factors affecting the efficient MO conversion and the selectivity

Cross metathesis (CM) reactions of methyl oleate (MO) with cis-4-octene (OC), cis-stilbene (CS) using RuCl2(PCy3)(IMesH2)(CHPh) [IMesH2 = 1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene; Cy = cyclohexyl] afforded CM products with high MO conversion and high selectivity under high molar (OC/MO, CS/MO) ratios; CM with cis-1,4-diacetoxy-2-butene also afforded metathesis products with high MO conversion under certain conditions. The efficient CM with allyltrimethylsilane proceeded with high activity, whereas the CM with glycidyl ether, β-pinene, and vanillylidenacetone proceeded with low MO conversion.

High Trans Kinetic Selectivity in Ruthenium-Based Olefin Cross-Metathesis through Stereoretention

The first kinetically controlled, highly trans-selective (>98%) olefin cross-metathesis reaction is demonstrated using Ru-based catalysts. Reactions with either trans or cis olefins afford products with highly trans or cis stereochemistry, respectively. This E-selective olefin cross-metathesis is shown to occur between two trans olefins and between a trans olefin and a terminal olefin. Additionally, new stereoretentive catalysts have been synthesized for improved reactivity. (Chemical Equation Presented).