10486-19-8

Usage

Uses

Used in Fragrance Industry:
Tridecanal is used as a fragrance ingredient for its ability to impart fresh nuances in the top note as well as in the dry-out of fragrance compositions. Its slightly citrus-like odor adds a pleasant and refreshing quality to various scent formulations.
Used in Chemical Analysis:
Tridecanal serves as a model compound in the nonradioactive assay/RP-HPLC-fluorescence analysis of aliphatic aldehydes, employing the Hantzsch reaction. This application is crucial for the study and detection of aliphatic aldehydes in various chemical and biological processes.
Used in Research and Development:
The chemical properties and occurrence of tridecanal make it a valuable compound for research and development purposes. Its study, particularly in the uptake of NO(3) on solid tridecanal, contributes to the understanding of its interactions and potential applications in various fields.

InChI:InChI=1/C16H16N2O2/c1-11-3-7-13(8-4-11)15(19)17-18-16(20)14-9-5-12(2)6-10-14/h3-10H,1-2H3,(H,17,19)(H,18,20)

Upstream product

• 112-70-9 tridecan-1-ol 
• 110023-68-2 C₂₇H₄₀OS₂ 
• 112-41-4 1-dodecene 
• 201230-82-2 carbon monoxide 
• 544-63-8 n-tetradecanoic acid 
• 64-18-6 formic acid 
• 17746-06-4 n-tridecanoyl chloride 
• 108-88-3 toluene 
• 15890-72-9 laurylmagnesium bromide 
• 242458-31-7 Dodecyl pyridin-2-yl ketone 
• 638-53-9 tridecanoic acid 
• 124-38-9 carbon dioxide 
• 142-84-7 di-n-propylamine 
• 1120-36-1 1-tetradecene 

Downstream Products

• 135838-73-2 2-Dodecyl-1,3-dimethyl-2,3-dihydro-1H-perimidine 
• 99814-65-0 pentadec-1-en-3-ol 
• 150252-78-1 6-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-dodecyl-2-methoxy-1,4-dihydro-pyrimidine-5-carboxylic acid benzyl ester 
• 154659-19-5 (2S,3R,4R)-1-(benzyloxy)-2-hexadecane-3,4-diol 
• 189106-84-1 (R)-5-((R)-1-Hydroxy-tridecyl)-1-((R)-2-methoxy-1-phenyl-ethyl)-1,5-dihydro-pyrrol-2-one 
• 189106-85-2 (S)-5-((S)-1-Hydroxy-tridecyl)-1-((R)-2-methoxy-1-phenyl-ethyl)-1,5-dihydro-pyrrol-2-one 
• 112-70-9 tridecan-1-ol 
• 211861-00-6 (S,S) thréo e.e. 90% (+ 40% érythro) 
• 612084-67-0 Carbonic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester (R)-(R)-1-(tetrahydro-furan-2-yl)-tridecyl ester 
• 612084-71-6 (+)-O-menthoxycarbonyl muricatacin 
• 848441-64-5 2-diethylamino-N-[2,6-dimethyl-3-tridecylamino-phenyl]-acetamide 
• 638-53-9 tridecanoic acid 

Relevant academic research and scientific papers

Hydroformylation of higher olefins in aqueous biphasic medium using rhodium-sulfoxantphos catalyst: Activity and selectivity study

Hydroformylation of higher olefins such as 1-hexene, 1-octene, 1-decene and 1-dodecene has been studied in an aqueous biphasic medium using water-soluble Rh-sulfoxantphos complex catalyst. The effect of temperature, presence of various co-solvents and concentration of co-solvent on the reaction rate and chemo and regioselectivity was investigated. N-Methyl pyrrolidone (NMP) was found to be the best co-solvent, which enhances the rate dramatically (4-96 fold) as compared to the reactions in aqueous-organic biphasic medium for hydroformylation of higher olefins. Catalyst recycle study was performed to check the leaching of metal in organic phase.

Pickering emulsions based on supramolecular hydrogels: Application to higher olefins' hydroformylation

Supramolecular hydrogels elaborated from a mixture of native α-cyclodextrin and poly(ethylene glycol)s in water proved to be effective media for higher olefins Rh-catalyzed hydroformylation due to the formation of Pickering emulsions.

Crucial role of additives in iridium-catalyzed hydroformylation

Abstract This paper presents the new highly selective iridium-catalyzed hydroformylation of 1-octene with an Ir(cod)(acac)/PPh3/salt catalyst system. The addition of inorganic salts such as LiCl suppresses the hydrogenation of 1-octene and increases the yield of desired hydroformylation products. Even low amounts of LiCl (LiCl/Ir = 2/1) significantly increase the chemoselectivity of aldehydes up to 94% with a 1-octene conversion of 90% within 7 h. This catalyst is applicable to other alkenes such as 1-pentene or 1-dodecene. The high selectivities and the remarkable activity of the optimized iridium catalyst are promising in terms of successfully implementing on an industrial scale in the future.

Thermal, Catalytic Conversion of Alkanes to Linear Aldehydes and Linear Amines

Alkanes, the main constituents of petroleum, are attractive feedstocks for producing value-added chemicals. Linear aldehydes and amines are two of the most important building blocks in the chemical industry. To date, there have been no effective methods for directly converting n-alkanes to linear aldehydes and linear amines. Here, we report a molecular dual-catalyst system for production of linear aldehydes via regioselective carbonylation of n-alkanes. The system is comprised of a pincer iridium catalyst for transfer-dehydrogenation of the alkane using t-butylethylene or ethylene as a hydrogen acceptor working sequentially with a rhodium catalyst for olefin isomerization-hydroformylation with syngas. The system exhibits high regioselectivity for linear aldehydes and gives high catalytic turnover numbers when using ethylene as the acceptor. In addition, the direct conversion of light alkanes, n-pentane and n-hexane, to siloxy-terminated alkyl aldehydes through a sequence of Ir/Fe-catalyzed alkane silylation and Ir/Rh-catalyzed alkane carbonylation, is described. Finally, the Ir/Rh dual-catalyst strategy has been successfully applied to regioselective alkane aminomethylation to form linear alkyl amines.

Analysis of the reaction network for the Rh-catalyzed hydroformylation of 1-dodecene in a thermomorphic multicomponent solvent system

The hydroformylation of 1-dodecene was studied using Rh(acac)(CO) 2 and a ligand as a catalyst in a thermomorphic multicomponent solvent (TMS) system consisting of N,N-dimethylformamide, decane and the olefin. High n-aldehyde/iso-aldehydes ratios were obtained with the bidentate phosphite ligand biphephos. In systematic preliminary investigations suitable catalyst/ligand-ratios and catalyst concentrations were determined. In order to derive a simplified reaction network, semi-batch experiments were performed measuring responses to perturbations of pressure and feed composition. From the results obtained the main branches of the reaction network could be identified comprising also isomerizations and hydrogenations of n- and iso-dodecenes. For this simplified reaction network a catalytic cycle is suggested providing the basis for the formulation of a more detailed mechanistic kinetic model.

Highly efficient heterogeneous hydroformylation over rh-metalated porous organic polymers: Synergistic effect of high ligand concentration and flexible framework

A series of diphosphine ligand constructed porous polymers with stable and flexible frameworks have been successfully synthesized under the solvothermal conditions from polymerizing the corresponding vinyl-functionalized diphosphine monomers. These insoluble porous polymers can be swollen by a wide range of organic solvents, showing similar behavior to those of soluble analogues. Rather than just as immobilizing homogeneous catalysts, these porous polymers supported with Rh species demonstrate even better catalytic performance in the hydroformylations than the analogue homogeneous catalysts. The sample extraordinary performance could be attributed to the combination of high ligand concentration and flexible framework of the porous polymers. Meanwhile, they can be easily separated and recycled from the reaction systems without losing any activity and selectivity. This excellent catalytic performance and easy recycling heterogeneous catalyst property make them be very attractive. These diphosphine ligand constructed porous polymers may provide new platforms for the hydroformylation of olefins in the future.

Enzyme Activity by Design: An Artificial Rhodium Hydroformylase for Linear Aldehydes

Artificial metalloenzymes (ArMs) are hybrid catalysts that offer a unique opportunity to combine the superior performance of natural protein structures with the unnatural reactivity of transition-metal catalytic centers. Therefore, they provide the prospect of highly selective and active catalytic chemical conversions for which natural enzymes are unavailable. Herein, we show how by rationally combining robust site-specific phosphine bioconjugation methods and a lipid-binding protein (SCP-2L), an artificial rhodium hydroformylase was developed that displays remarkable activities and selectivities for the biphasic production of long-chain linear aldehydes under benign aqueous conditions. Overall, this study demonstrates that judiciously chosen protein-binding scaffolds can be adapted to obtain metalloenzymes that provide the reactivity of the introduced metal center combined with specifically intended product selectivity.

Radical carbonylations using a continuous microflow system

Radical-based carbonylation reactions of alkyl halides were conducted in a microflow reactor under pressurized carbon monoxide gas. Good to excellent yields of carbonylated products were obtained via radical formylation, carbonylative cyclization and threecomponent coupling reactions, using tributyltin hydride or TTMSS as a radical mediator.

Rhodium nanoparticles as catalysts in the hydroformylation of 1-dodecene and their recycling in thermomorphic solvent systems

Rhodium nanoparticles of about 3 nm in size were provided in stabilizing polar solvents. These nanoparticles were used in hydroformylation reactions of higher alkenes; 1-dodecene was used as a model substance. With a metal/substrate ratio of 1:1000, a 97% yield of aldehydes was achieved and an n/iso ratio of 72:28 was obtained. The addition of the ligand biphephos decelerated the reaction, but high n/iso ratios of up to 96:4 were achieved. For the first time, an effective catalyst recycling of these long-term stable nanoparticles in a thermomorphic multicomponent solvent (TMS) system was performed. The catalyst phase was recycled for three runs without any evident loss in activity. TEM images proved that after the recycling runs rhodium nanoparticles were still the active catalyst.

Synthesis of the novel ligand tris-(3,4-dimethoxylphenyl) phosphine and its catalytic performance in 1-dodecene hydroformylation

Tris-(3,4-dimethoxylphenyl)phosphine (TDMOPP) was synthesized and used as a ligand for the homogenous hydroformylation of 1-dodecene. The effects of the P/Rh molar ratio and reaction temperature on the activity and regioselectivity were investigated. The results showed that the activity of TDMOPP was about two times higher than that of the traditional triphenylphosphine at a low P/Rh and temperature.