24753-49-9

Usage

Uses

Used in Plastics and Polymers Industry:
9-Octadecenedioic acid, dimethyl ester, (9E)is used as a plasticizer for enhancing the flexibility and workability of plastics and polymers during manufacturing processes. Its incorporation into these materials results in improved physical properties and performance characteristics.
Used as a Lubricant:
In the lubricants industry, 9-Octadecenedioic acid, dimethyl ester, (9E)serves as a high-quality lubricant. It reduces friction between moving parts, thereby increasing the efficiency and lifespan of machinery and equipment.
Used in Chemical Production:
9-Octadecenedioic acid, dimethyl ester, (9E)is utilized as an intermediate in the synthesis of other chemicals. Its unique structure and properties make it a valuable component in the production of various industrial and consumer products, contributing to the development of new and innovative applications.

Upstream product

• 129010-10-2 9-octadecyne-1,18-dioic acid dimethyl ester 
• 1931-63-1 methyl ester of azelaic acid aldehyde 
• 67878-16-4 (8-methoxycarbonyloctyl)triphenylphosphonium bromide 
• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 19754-58-6 2-dec-9-ynyloxy-tetrahydro-pyran 
• 50816-19-8 8-bromooctanol 
• 112-62-9 Methyl oleate 
• 107-13-1 acrylonitrile 
• 74-85-1 ethene 
• 123-99-9 azelaic acid 
• 34957-73-8 methyl 9-hydroxynonanoate 
• 2104-19-0 azelaic monomethyl ester 
• 2462-84-2 methyl (9E)-octadec-9-enoate 
• 25601-41-6 methyl 9-decenoate 

Downstream Products

• 25601-41-6 methyl 9-decenoate 
• 1046470-12-5 methyl 10-cyano-dec-9-enoate 
• 13481-97-5 dimethyl 9-octadecen-1,18-dioate 
• 20701-67-1 9-octadecenedioic acid 
• 20701-68-2 (9Z)-octadec-9-enedioic acid 
• 123-99-9 azelaic acid 
• 2104-19-0 azelaic monomethyl ester 
• 347308-58-1 dimethyl 8,8'-(oxirane-2,3-diyl)dioctanoate 
• 67136-05-4 dimethyl 9-hydroxy-10-oxooctadecanedioate 
• 67852-29-3 dimethyl 9,10-dihydroxyoctadecanedioate 
• 28691-27-2 methyl 11-aminoundecanoate 
• 4088-26-0 9-aminopelargonic methyl ester 

Relevant academic research and scientific papers

TUNGSTEN IMIDO ALKYLIDENE O-BITET AND O-BINOL COMPLEXES AND USE THEREOF IN OLEFIN METATHESIS REACTIONS

The invention relates to tungsten imido alkylidene compounds bearing a ligand derived from a 1,1'-binaphthyl-2-ol or a 5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2- ol which bind to tungsten in its olate-form via proton abstraction from the phenolic OH group. The complexes may be used in various olefinic metathesis reactions, preferably ethenolysis and cross-metathesis of unsaturated fatty acid esters, and ring-closing metathesis reactions.

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.

Cis-Dichloro Sulfoxide Ligated Ruthenium Metathesis Precatalysts

Novel sulfoxide-ligated ruthenium complexes were prepared by reacting second-generation metathesis precatalysts with p-toluenesulfonyl chloride in the presence of a small excess of sulfoxide. (SIMes)Ru(S-DMSO)(Ind)Cl2 (M54) and (SIMes)Ru(S-DMSO)(CHPh)Cl2 (M54a) were characterized crystallographically and, in agreement with NMR spectroscopy, were found to adopt an unusual cis-dichloro configuration. Despite having traditionally latent geometry, the new complexes were found to be highly reactive precatalysts for routine metathesis transformations. Additionally, the robustness, scalability, and industrial utility of M54 as a ruthenium synthon are demonstrated.

In Situ Generation of Ru-Based Metathesis Catalyst. A Systematic Study

A systematic study for the in situ generation of Ru-based metathesis catalysts was described. Assembly of commercially available and inexpensive reagents [Ru(p-cymene)Cl2]2, SIPr·HCl, and n-BuLi led to the formation of 18 electron arene-ruthenium complexes that, in the presence of additives such as alkynes, cyclopropenes, and diazoesters, generated highly selective and efficient catalytic systems applicable to a variety of olefin metathesis transformations. Notably, we were able to achieve a productive TON of 4500 for the self-metathesis of methyl oleate, a reaction which could be easily upscaled to 2 kg.

Fluoro-imidazopyridinylidene Ruthenium Catalysts for Cross Metathesis with Ethylene

A series of ruthenium metathesis catalysts bearing fluorinated imidazo[1,5-a]pyridin-3-ylidene carbenes (F-ImPy) were developed for ethenolysis (cross metathesis with ethylene) of methyl oleate. X-ray crystal structure analysis shows Ru-F interaction, and this fluorine substitution appears to be pivotal to have stable ImPy-Ru precatalysts. Ligand structure was varied for high catalyst activity and cross metathesis selectivity in ethenolysis reaction. F-ImPy-Ru catalysts showed high selectivity in ethenolysis of methyl oleate and thermal robustness under an ethylene atmosphere.

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 Application of Stereoretentive Ruthenium Catalysts on the Basis of the M7 and the Ru-Benzylidene-Oxazinone Design

A series of new stereoretentive ruthenium catalysts bearing the dithiocatecholate ligand was synthesiszed on the basis of the M7 and Ru-benzylidene-oxazinone design. The activity of the catalysts was tested in ring-opening cross-metathesis reactions, ring

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 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.

METHODS OF MAKING OLEFINIC E- AND Z-ISOMERS

Method of making a second olefin using a first olefin, comprising steps (A) and (B): (A) performing a metathesis reaction with the first olefin in the presence of a metal complex configured to catalyse said metathesis reaction; (B) epoxidizing an olefin contained in the reaction mixture obtained in step (A) to form an epoxide; and deoxygenizing said epoxide to form said second olefin.