22915-49-7

Usage

Uses

Methyl 11-cyanoundecanoate is a precursor for many reactions.

Upstream product

• 67-56-1 methanol 
• 27335-49-5 (Z)-2-hydroxyiminocyclododecanone 
• 68226-33-5 2,2-dimethoxycyclododecanone oxime 
• 24724-07-0 methyl 11-hydroxyundecanoate 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 74-90-8 hydrogen cyanide 
• 111-81-9 Methyl 10-undecenoate 
• 151-50-8 potassium cyanide 
• 51238-63-2 (E)-1-methoxycyclododecene 
• 830-13-7 cyclododecanone 
• 112-38-9 10-undecenoic acid 
• 14811-73-5 10-oxo-decanoic acid methyl ester 
• 1346519-50-3 C₁₃H₂₁NO₂ 
• 53179-04-7 undec-10-enenitrile 

Downstream Products

• 693-23-2 1,12-dodecanedioic acid 
• 22543-30-2 12-aminolauric acid hydrogen chloride salt 

Relevant academic research and scientific papers

Preparation of nitriles by the modification of Mitsunobu-Wilk procedure III carbon elongation of hydroxy esters

An efficient one-step procedure for the conversion of hydroxy esters into the corresponding nitrile esters using triphenylphosphine (PPh3)-diethyl azodicarboxylate (DEAD) in the presence of acetone cyanohydrin is described.

Polyamide precursors from renewable 10-undecenenitrile and methyl acrylate via olefin cross-metathesis

The ruthenium-catalyzed cross-metathesis of the unsaturated fatty acid derivative 10-undecenenitrile 1 arising from castor oil with methyl acrylate produces a C12 nitrile ester with high turnover number. This product has potential as a new bio-sourced intermediate for the production of polyamides. This route competes favourably with the reverse cross-metathesis of methyl 10-undecenoate with acrylonitrile leading to the same C12 α,ω-amino ester 7 after hydrogenation of the carbon-carbon double bond and the nitrile functionality.

One-pot synthesis of aldoximes from alkenes: Via Rh-catalysed hydroformylation in an aqueous solvent system

Aldoxime synthesis directly starting from alkenes was successfully achieved through the combination of hydroformylation and subsequent condensation of the aldehyde intermediate with aqueous hydroxylamine in a one-pot process. The metal complex Rh(acac)(CO)2 and the water-soluble ligand sulfoxantphos were used as the catalyst system, providing high regioselectivities in the initial hydroformylation. A mixture of water and 1-butanol was used as an environmentally benign solvent system, ensuring sufficient contact of the aqueous catalyst phase and the organic substrate phase. The reaction conditions were systematically optimised by Design of Experiments (DoE) using 1-octene as a model substrate. A yield of 85% of the desired linear, terminal aldoxime ((E/Z)-nonanal oxime) at 95% regioselectivity was achieved. Other terminal alkenes were also converted successfully under the optimised conditions to the corresponding linear aldoximes, including renewable substrates. Differences of the reaction rate have been investigated by recording the gas consumption, whereby turnover frequencies (TOFs) >2000 h-1 were observed for 4-vinylcyclohexene and styrene, respectively. The high potential of aldoximes as platform intermediates was shown by their subsequent transformation into the corresponding linear nitriles using aldoxime dehydratases as biocatalysts. The overall reaction sequence thus allows for a straightforward synthesis of linear nitriles from alkenes with water being the only by-product, which formally represents an anti-Markovnikov hydrocyanation of readily available 1-alkenes.

PREPARATION OF AMINO ACIDS AND AMINO ACID DERIVATIVES

The invention relates to a method for synthesizing amino acids or amino acid derivatives involving cross metathesis of functionalized olefins and a tandem amination-reduction process. Amino acids and amino acid derivatives present many interesting physical and chemical properties finding many uses in the automotive, fuel, electronic, and textile industries.

Cross-metathesis approach to produce precursors of nylon 12 and nylon 13 from microalgae

A two-step synthesis for producing methyl 12-aminododecanoate and 13-aminotridecanoate, the precursors of nylon 12 and nylon 13, from methyl oleate is described. First, methyl 11-cyano-9-undecenoate or 12-cyano-9-dodecenoate were prepared by cross metathesis of methyl oleate with either allyl cyanide or homoallyl cyanide, respectively. Subsequently, all the unsaturation of the two intermediates was hydrogenated to deliver the final products. This method represents the first synthesis of nylon 12 and 13 precursors from methyl oleate, an ester of an abundant and renewable natural fatty acid present in vegetable oil or microalgae. It also represents the shortest synthesis of nylon precursors from fatty acids, and as demonstrated in this study, can be directly applied to crude fatty acid methyl ester extracts from microalgae.

Divergent process for C10, C11 and C12 ω-amino acid and α,ω-dicarboxylic acid monomers of polyamides from castor oil as a renewable resource

Polyamides have great potentials for diverse applications and the present production of their monomers mostly relies on resources from fossil fuel. Starting from undecylenic acid, a natural resource, we have developed both divergent and efficient processes for C10, C11 and C 12 ω-amino acid and α,ω-dicarboxylic acid monomers of the polyamides.

Tandem catalytic acrylonitrile cross-metathesis and hydrogenation of nitriles with ruthenium catalysts: Direct access to linear α,ω- aminoesters from renewables

Fraternité, Solidarité & complémentarité en Catalyse: Tandem alkene cross-metathesis of acrylonitrile with long-chain alkene and hydrogenation catalysis is performed by using a single ruthenium-alkylidene catalyst precursor. The protocol allows the catalytic transformation of unsaturated fatty acids, derivatives of plant oils, into α,ω-aminoesters. A key step involves the reduction of nitrile-ester intermediates into aminoesters, the precursors of polyamides, with alkene metathesis catalyst residue under mild conditions. Copyright

Renewable materials as precursors of linear nitrile-acid derivatives via cross-metathesis of fatty esters and acids with acrylonitrile and fumaronitrile

The cross-metathesis of fatty acids and esters, as renewable raw materials, with acrylonitrile and fumaronitrile is presented. The cross-metathesis reactions of both terminal and internal double bond containing compounds were performed using a ruthenium c

Application of chelating diphosphine ligands in the nickel-catalysed hydrocyanation of alk-1-enes and ω-unsaturated fatty acid esters

The hydrocyanation of alk-1-enes and ω-unsaturated fatty acid esters using zerovalent nickel complexes yields the corresponding nitriles and cyanoesters, which can be useful starting materials in organic synthesis.