22092-54-2

Usage

Uses

Used in the Food Industry:
2-Ethylvaleraldehyde is used as a flavoring agent for its strong, characteristic aroma, enhancing the taste and smell of various food products.
Used in the Fragrance Industry:
It is employed as a component in perfumes, leveraging its pungent odor to contribute to the creation of complex and appealing scents.
Used as a Chemical Intermediate:
2-Ethylvaleraldehyde is utilized in the synthesis of other compounds, playing a crucial role in chemical manufacturing processes.
Used in the Printing and Dyeing Industries:
It is used as a solvent in these industries, aiding in the application and fixation of dyes and inks onto various substrates.

InChI:InChI=1/C7H14O/c1-3-5-7(4-2)6-8/h6-7H,3-5H2,1-2H3

Upstream product

• 16403-08-0 (E)-2-ethyl-pent-2-en-1-ol 
• 5204-80-8 2-ethylpent-4-enal 
• 110-62-3 pentanal 
• 75-03-6 ethyl iodide 
• 53516-60-2 butyl-isobutyl-pent-1-enyl-amine 
• 925-90-6 ethylmagnesium bromide 
• 123-72-8 butyraldehyde 
• 122-51-0 orthoformic acid triethyl ester 
• 592-41-6 1-hexene 
• 201230-82-2 carbon monoxide 
• 592-43-8 2-hexene 
• 13269-52-8 trans-3-Hexene 
• 4050-45-7 trans-2-hexene 
• 928-49-4 hex-3-yne 

Relevant academic research and scientific papers

Method for preparing aldehyde through hydroformylation of internal olefin

The invention provides a method for preparing aldehyde through hydroformylation of internal olefin. The preparation method is characterized by comprising the following steps: adding a water-soluble rhodium compound, a water-soluble diphosphine ligand, an additive, deionized water and internal olefin into a reaction kettle equipped with a stirrer and a thermocouple; carrying out replacing 3-5 timesby using synthesis gas formed by mixing hydrogen and carbon monoxide according to a volume ratio of 1: 1; carrying out pressurizing to 1.0-5.0 MPa; conducting a reaction for 2-10 hours at a temperature of 60-120 DEG C; and conducting cooling, taking out a reaction product, and performing separating to obtain the product aldehyde.

Biphase hydroformylation catalyzed by rhodium in combination with a water-soluble pyridyl-triazole ligand

[RhCl(COD)]2in combination with a water soluble sulphonated pyridyl-triazolyl N,N-bidentate ligand efficiently catalyzes styrene and 1-hexene hydroformylation in water/organic solvent biphasic systems. The catalyst displays a good activity affording mixtures of linear and branched aldehydes with complete chemoselectivity. The aqueous catalytic phase may be recycled four times giving complete substrate conversion by 18 h. Mercury-poisoning experiments and transmission electron microscopy indicate that, after the first catalytic run, rhodium is present in the aqueous phase in nanoparticle form.

Enhancing catalytic performance of activated carbon supported Rh catalyst on heterogeneous hydroformylation of 1-hexene via introducing surface oxygen-containing groups

Activated carbon supported rhodium (Rh/AC) catalysts with different amounts of oxygen-containing functional groups were prepared by nitric acid (HNO3) treatment at varied temperatures. Thermal analyses of Rh/AC catalysts with or without this acidic treatment were characterized by thermogravimetric analysis (TGA) and temperature programmed desorption (TPD). The change of surface oxygen-containing functional groups was characterized by Fourier transform infrared spectrometry (FTIR) and X-ray photoelectron spectroscopy (XPS). These characterization results indicated that the amount of oxygen-containing functional groups increased with the treatment temperature. The influence of these oxygen-containing functional groups on the products selectivities in heterogeneous hydroformylation reaction was investigated in detail. These abundant functional groups were benefited to improve the selectivity of n-heptanal, resulting in higher n/i (normal to iso) ratio of heptanal. The Rh/AC catalyst being treated at 80?°C had the highest n/i ratio of 2.3, due to the maximum amount of oxygen-containing functional groups, which was almost double to that of raw Rh/AC catalyst. Moreover, abundant functional groups on catalyst suppressed hydrogenation of hexene, decreasing the selectivity of hexane from 4.9% of raw Rh/AC to 0.2%. These findings disclosed that these oxygen-containing functional groups on catalysts played an extremely important role in improving the catalytic performance of heterogeneous hydroformylation reaction, providing a new viewpoint for the studies on heterogeneous hydroformylation.

Active and regioselective rhodium catalyst supported on reduced graphene oxide for 1-hexene hydroformylation

Alkene hydroformylation with syngas (CO + H2) to produce aldehydes is one of the most important chemical reactions. However, designing heterogeneous catalysts to realize comparable performance with mature homogeneous catalysts is challenging. In this report, a reduced graphene oxide (RGO) supported rhodium nanoparticle (Rh/RGO) catalyst was successfully prepared via a one-pot liquid-phase reduction method and first applied in 1-hexene hydroformylation. 1-Hexene hydroformylation reaction under different reaction conditions with this Rh/RGO catalyst was investigated in detail. Low reaction temperature and short reaction time effectively enhanced the n/i (normal to iso) ratio of heptanal in the products. The catalytic performance of the Rh/RGO catalyst was also compared with those of Rh supported on other carbon materials, including activated carbon and carbon nanotubes (Rh/AC and Rh/CNTs). The results showed that the Rh/RGO catalyst exhibited the highest 1-hexene conversion and the largest n/i ratio of 4.0 among the tested catalysts. The special 2D nanosheet structure of the Rh/RGO catalyst, rather than the 3D porous and 1D nanotube structures of Rh/AC and Rh/CNTs, respectively, principally contributed to its excellent catalytic performance. These findings disclosed that reduced graphene oxide could be a promising catalyst support for designing heterogeneous hydroformylation catalysts.

On rhodium complexes bearing H-spirophosphorane derived ligands: Synthesis, structural and catalytic properties

We investigated the coordination properties of H-spirophosphoranes towards rhodium ion. Symmetrical phosphorus ligands: HP(OCH2CH 2NH)2 L1, HP(OCH2CM-2NH)2 L2, HP(OCMe2CMe 2O)2 L3, HP(OC6H4NH)2 L4, and unsymmetrical phosphorus ligands: HP(OCMe2CMe2O)(OCH2CM-2NH) L5, HP(OCMe2CMe2O)(OC6H4NH) L6 were found to coordinate to rhodium precursor [Rh(CO)2Cl]2 exclusively in protonated k2-P,E (E =N, O) bidentate fashion, yielding complexes [Rh(CO)ClL] 1-6. The complexes were characterised by spectroscopic methods. The molecular structures of the ligand L6 complexes 3, 5 and 6 were determined by single-crystal X-ray diffraction. The catalytic activity of the complexes was determined in hydroformylation reaction of 1-hexene. Complexes 1 and 2 appeared to be active in isomerisation reactions yielding 76 and 62% of 2-hexene. When used with six-fold excess of triphenylphosphite P(OPh)3 as a modified ligand, the most active catalyst 1 in hydroformylation reaction produced 66% of aldehydes and 22% of 2-hexene.

Microencapsulated ruthenium catalyst for the hydroformylation of 1-hexene

A ruthenium complex [Ru(CO)3Cl2]2 microencapsulated into poly(4-vinylpyridine) (P4VP) cross-linked with 25% divinylbenzene (DVB) was developed as a new catalyst for the hydroformylation of 1-hexene. The highest catalytic activity with the 93% total conversion, and with yields of 44% aldehydes and 26% alcohols was achieved at 423 K. Typically, the polymer capsules are used at temperatures below 373 K. The DVB cross-linked P4VP capsules were, however, thermally stable at 423 K and could be recycled at least four times with moderate loss of catalytic activity. The catalysts were characterized by SEM, ICP-MS, and FT-IR.

Coordination studies on supramolecular chiral ligands and application in asymmetric hydroformylation

In this study we introduce a series of monodentate pyridine-based ligands for which the phosphorus coordination mode to rhodium can be controlled by the binding of ZnII-templates to the pyridyl group. A series of monodentate phosphoroamidite and phosphite ligands have been prepared and studied under hydroformylation conditions by in situ high-pressure NMR and IR techniques. These studies reveal the exclusive formation of rhodium hydride complexes in which the phosphorus atom of the ligand resides in an axial position, trans to the hydride, but only after addition of Zn II-template. In the absence of these templates the usual mono-coordinated rhodium hydrido complexes are formed, with the phosphorus ligated in the equatorial plane, cis to the hydride. The catalytic performance of these complexes is evaluated in asymmetric hydroformylation of unfunctionalised internal alkenes in which the supramolecular change is reflected in higher activity and selectivity.

Selective hydroformylation of 1-hexene to branched aldehydes using rhodium complex of modified bulky phosphine and phosphite ligands

The selective hydroformylation of 1-hexene to branched aldehydes was investigated using rhodium complex of tri-1-naphthylphosphine PNp3 and tri-1-naphthylphosphite P(ONp)3. The PNp3 and P(ONp)3 ligands having more steric nature than PPh3 enhanced the formation of branched aldehydes at 110 °C and 4.0 MPa syngas pressure. The branched aldehyde selectivity increased remarkably (82%) by adding P(ONp)3 as auxiliary ligand in Rh/PNp3 catalyzed hydroformylation of 1-hexene. The high selectivity for the branched aldehydes is due to rapid alkene isomerization producing internal alkenes followed by hydroformylation to yield branched aldehydes.

Hydroformylation of alkenes using heterogeneous catalyst prepared by intercalation of HRh(CO)(TPPTS)3 complex in hydrotalcite

Intercalation of HRh(CO)(TPPTS)3 complex into the interlayer space of hydrotalcite was carried out to prepare an eco-friendly heterogeneous hydroformylation catalyst. Intercalated catalyst was characterized by 31P NMR, P-XRD, FT-IR, SEM and surface area measurements. Catalytic activity of intercalated catalyst [HT(3.5)-INT] was evaluated for hydroformylation of linear alkenes of varied carbon number from C5 to C13 as well as cyclic alkenes. Selectivity of the aldehydes was observed to decrease with increase in the carbon chain length of linear alkenes. Effect of reaction parameters on catalytic activity of intercalated catalyst was studied by varying the catalyst amount, 1-hexene concentration, reaction temperature, partial pressure of carbon monoxide and hydrogen for hydroformylation of 1-hexene. The catalyst was re-cycled up to five times without significant loss in the alkene conversion and selectivity of aldehydes.

Aqueous-biphasic hydroformylation of alkenes promoted by "weak" surfactants

The aqueous-biphasic hydroformylation of higher alkenes catalyzed by Rh/TPPTS has been carried out in the presence of imidazolium, pyridinium and triethylammonium salts. High reaction rates are achieved with imidazolium and triethylammonium salts provided that their alkyl "tail" is ≥C 8. Fast and complete phase separation, and good retention of the metal in the aqueous phase could be achieved with an octyl "tail". Imidazolium salts were found to give the highest rate enhancement. The nature of the anion showed a moderate influence on the reaction. Evidence suggests that the additive can act as weak surfactant allowing emulsions to be formed and broken by simply switching the stirring on and off.