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Usage

Uses

Used in Flavor and Fragrance Industry:
(9Z)-Undec-9-enenitrile is used as a flavoring agent and fragrance ingredient for its fruity scent, contributing to the production of perfumes, soaps, and other personal care products.
Used in Pest Control:
(9Z)-Undec-9-enenitrile is used as an insecticidal agent in the formulation of insect repellents and as an ingredient in pest control products, thanks to its insecticidal properties.
Used in Organic Synthesis:
(9Z)-Undec-9-enenitrile serves as a key intermediate in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals, due to its chemical structure and reactivity.
Used in Industrial and Commercial Applications:
This chemical compound is utilized in various industrial and commercial applications, taking advantage of its relatively stable nature and low water solubility, which makes it suitable for a wide range of uses.

Upstream product

• 53179-04-7 undec-10-enenitrile 
• 201230-82-2 carbon monoxide 

Relevant academic research and scientific papers

METHOD FOR THE CONTROLLED HYDROFORMYLATION AND ISOMERIZATION OF A NITRILE/ESTER/OMEGA UNSATURATED FATTY ACID

A method to synthesize a fatty nitrile/ester aldehyde comprising the following steps: 1) hydroformylation of a ω-unsaturated fatty nitrile/ester/acid substrate under particular conditions of partial pressure, temperature, reaction time, conversion rate of the ω-unsaturated fatty nitrile/ester/acid reactant, catalyst, [substrate]/[metal] molar ratio and [ligand]/[metal] molar ratio so as after the reaction to obtain: a hydroformylation product comprising at least one fatty nitrile/ester/acid aldehyde of formula: OHC—(CH2)r+2—R, andan isomerate comprising at least one fatty nitrile/ester/acid isomer with internal unsaturation in which at least 80% of the internal isomer(s) of the isomerate are formed of the ω-1 unsaturated isomer of formula CH3—CH═CH—(CH2)r?1—R; followed by:2) separation and recovery of the fatty nitrile/ester/acid aldehyde and of the isomerate.

Rhodium versus iridium catalysts in the controlled tandem hydroformylation-isomerization of functionalized unsaturated fatty substrates

The hydroformylation of 10-undecenitrile (1) and related unsaturated fatty substrates (H2C=CH(CH2)7CH2R; R=CO2Me, CH2Br, CHO) has been studied with rhodium, iridium, ruthenium, and palladium biphephos catalysts. The reactions proceeded effectively with all four systems, with high selectivities for the linear aldehyde (ratio of linear/branched aldehydes=99:1). The biphephos-bis[chloro(cyclooctadiene)iridium] system showed a non-optimized hydroformylation turnover frequency (TOFHF) of 770h-1 that was only approximately 5times lower than that of the rhodium-based system (TOFHF=3320h-1); the palladium and ruthenium biphephos systems were less active (TOFHF=210 and 310h-1, respectively). Upon recycling, remarkable productivities were achieved in both cases (TON≈58-000mol(1/1-int)-mol(Ir)-1 and 250-000mol(1/1-int)-mol(Rh)-1, in which int=internal olefin). Competitive isomerization of terminal to internal olefins occurred with these catalysts. Iridium biphephos systems allowed slightly better control of the distribution of the internal isomers than the rhodium biphephos catalyst, with higher ratios of 9-/8-undecenitrile (1-int). Place your bets now: Iridium-biphephos catalysts are highly effective in the controlled tandem isomerization-hydroformylation of 10-undecenitrile and related functionalized unsaturated fatty substrates.