80466-34-8

Usage

Uses

Used in Flavor and Fragrance Industry:
2,4-Hexadienal is used as a flavoring agent for its distinctive and strong odor, contributing to the creation of various scents and tastes in the flavor and fragrance industry.
Used in Chemical Synthesis:
2,4-Hexadienal serves as an important intermediate in the synthesis of a range of organic compounds, playing a crucial role in the development of new chemical products.
Used in Food Additive Production:
2,4-Hexadienal is utilized in the production of food additives, enhancing the taste and aroma of various food products while ensuring their quality and safety.
Used in Pharmaceutical Industry:
2,4-Hexadienal is employed in the pharmaceutical sector for the synthesis of different medicinal compounds, contributing to the development of new drugs and treatments.
Used in Polymer and Resin Manufacturing:
Due to its high reactivity, 2,4-Hexadienal is used as a building block in the manufacturing of polymers, resins, and other industrial products, enhancing their properties and performance.

InChI:InChI=1/C6H8O/c1-2-3-4-5-6-7/h2-6H,1H3/b3-2-,5-4+

Upstream product

• 4540-33-4 piperdinium acetate 
• 75-07-0 acetaldehyde 
• 123-73-9 crotonaldehyde 
• 91001-07-9 (E)-hexa-1,4-dien-3-ol 
• 110-89-4 piperidine 
• 64-17-5 ethanol 
• 50-00-0 formaldehyd 
• 1388156-98-6 HDEGP 
• 123-38-6 propionaldehyde 
• 147-85-3 L-proline 
• 111-28-4 2,4-hexadiene-1-ol 
• 71-43-2 benzene 
• 25724-11-2 1.1.3.5-tetramethoxy-hexane 
• 7664-93-9 sulfuric acid 

Downstream Products

• 27310-22-1 1,1-diethoxy-2,4-hexadiene 
• 117679-33-1 (3E,5Z)-2-(Allyl-phenyl-amino)-hepta-3,5-dienenitrile 
• 1482-91-3 octa-1,3,5,7-tetraene 
• 1258958-61-0 (4E,6E)-1-phenyl-3-trimethylsilyloxy-4,6-octadien-1-one 
• 1449136-12-2 C₂₅H₂₃BrN₂O₂ 

Relevant academic research and scientific papers

Synthesis of α,β- and β-Unsaturated Acids and Hydroxy Acids by Tandem Oxidation, Epoxidation, and Hydrolysis/Hydrogenation of Bioethanol Derivatives

We report a reaction platform for the synthesis of three different high-value specialty chemical building blocks starting from bio-ethanol, which might have an important impact in the implementation of biorefineries. First, oxidative dehydrogenation of ethanol to acetaldehyde generates an aldehyde-containing stream active for the production of C4 aldehydes via base-catalyzed aldol-condensation. Then, the resulting C4 adduct is selectively converted into crotonic acid via catalytic aerobic oxidation (62 % yield). Using a sequential epoxidation and hydrogenation of crotonic acid leads to 29 % yield of β-hydroxy acid (3-hydroxybutanoic acid). By controlling the pH of the reaction media, it is possible to hydrolyze the oxirane moiety leading to 21 % yield of α,β-dihydroxy acid (2,3-dihydroxybutanoic acid). Crotonic acid, 3-hydroxybutanoic acid, and 2,3-dihydroxybutanoic acid are archetypal specialty chemicals used in the synthesis of polyvinyl-co-unsaturated acids resins, pharmaceutics, and bio-degradable/ -compatible polymers, respectively.

Ethanol to Butanol Conversion over Bifunctional Zeotype Catalysts Containing Palladium and Zirconium

Abstract: A study of the kinetics of ethanol conversion in the presence of Zr-containing zeolites BEA doped with palladium particles has revealed the order of formation of the main reaction products. It has been shown that the primary processes are ethanol dehydrogenation to acetaldehyde on Pd sites and ethanol dehydration to diethyl ether on the acid sites of the catalyst. After that, acetaldehyde undergoes the aldol–croton condensation reaction to form crotonal, which is hydrogenated to butanol on the metal sites. Butanol, in turn, is dehydrated into butenes, which undergo hydrogenation to butane. The presence of hydrogen in the gas phase leads to the displacement of ethanol from the metal surface and prevents the formation of surface carbonates and acetates. It has been found that hydrogen significantly accelerates ethanol dehydration owing to a decrease in the activation energy, which can be attributed to hydrogen spillover to the zeolite. The addition of water inhibits all acid-catalyzed reactions owing to competitive adsorption on acid sites and thereby decreases the butanol yield and the ethanol conversion.

An Engineered Alcohol Oxidase for the Oxidation of Primary Alcohols

Structure-guided directed evolution of choline oxidase has been carried out by using the oxidation of hexan-1-ol to hexanal as the target reaction. A six-amino-acid variant was identified with a 20-fold increased kcat compared to that of the wild-type enzyme. This variant enabled the oxidation of 10 mm hexanol to hexanal in less than 24 h with 100 % conversion. Furthermore, this variant showed a marked increase in thermostability with a corresponding increase in Tm of 20 °C. Improved solvent tolerance was demonstrated with organic solvents including ethyl acetate, heptane and cyclohexane, thereby enabling improved conversions to the aldehyde by up to 30 % above conversion for the solvent-free system. Despite the evolution of choline oxidase towards hexan-1-ol, this new variant also showed increased specific activities (by up to 100-fold) for around 50 primary aliphatic, unsaturated, branched, cyclic, benzylic and halogenated alcohols.

Structure-Guided Evolution of Aryl Alcohol Oxidase from Pleurotus eryngii for the Selective Oxidation of Secondary Benzyl Alcohols

Aryl alcohol oxidase (AAO) is a fungal flavoenzyme capable of oxidizing aromatic primary alcohols into their correspondent aldehydes through a stereoselective hydride abstraction. Unfortunately, this enzyme does not act on secondary benzyl alcohols in racemic mixtures due to the strict control of substrate diffusion and positioning at the active site restricted to primary benzyl alcohols. Here we describe the engineering of AAO from Pleurotus eryngii to oxidize chiral benzyl alcohols with high enantioselectivity. The secondary benzyl alcohol oxidase was remodeled at the active site through four cycles of structure-guided evolution, including a final step of in vivo site-directed recombination to address the positive epistatic interactions between mutations. The final variant, with five substitutions and a renovated active site, was characterized at biochemical and computational level. The mutational sculpting helped position the bulkier (S)-1-(p-methoxyphenyl)-ethanol, improving the mutant's catalytic efficiency by three orders of magnitude relative to the native enzyme while showing a high enantioselectivity (ee >99%). As a promising candidate for racemic resolution, this evolved secondary benzyl alcohol oxidase maintained its natural stereoselective mechanism while displaying activity on several secondary benzyl alcohols. (Figure presented.).

Catalytic Reactions of Homo- and Cross-Condensation of Ethanal and Propanal

Abstract: Processes of catalytic homocondensation of propanal and its cross-condensation with ethanal and methanal in the presence of aniline and amino acids have been studied. The dependence of the conversion of the reactants and selectivity of the homo/heterocondensation process on the catalyst nature and temperature has been revealed. It has been shown that the maximum acrolein selectivity is reached in the case of using benzoyl-substituted derivatives in water, with the proportion of the products of further condensation decreasing. The selectivity for the ethanal homocondensation product 2-butenal decreases simultaneously as a result of the formation of linear and branched oligomers of successive condensation.

Formation Pathways toward 2- and 4-Methylbenzaldehyde via Sequential Reactions from Acetaldehyde over Hydroxyapatite Catalyst

Condensation reactions of biomass derived C2 and C4 aldehydes form both ortho- and para-tolualdehydes (2-MB and 4-MB, respectively). The complete reaction network and the detailed mechanisms, however, have not been fully described. H

Synthesis of C4 and C8 Chemicals from Ethanol on MgO-Incorporated Faujasite Catalysts with Balanced Confinement Effects and Basicity

A new type of catalyst has been designed to adjust the basicity and level of molecular confinement of KNaX faujasites by controlled incorporation of Mg through ion exchange and precipitation of extraframework MgO clusters at varying loadings. The catalytic performance of these catalysts was compared in the conversion of C2 and C4 aldehydes to value-added products. The product distribution depends on both the level of acetaldehyde conversion and the fraction of magnesium as extraframework species. These species form rather uniform and highly dispersed nanostructures that resemble nanopetals. Specifically, the sample containing Mg only in the form of exchangeable Mg2+ ions has much lower activity than those in which a significant fraction of Mg exists as extraframework MgO. Both the (C6+C8)/C4 and C8/C6 ratios increase with additional extraframework Mg at high acetaldehyde conversion levels. These differences in product distribution can be attributed to 1) higher basicity density on the samples with extraframework species, and 2) enhanced confinement inside the zeolite cages in the presence of these species. Additionally, the formation of linear or aromatic C8 aldehyde compounds depends on the position on the crotonaldehyde molecule from which abstraction of a proton occurs. In addition, catalysts with different confinement effects result in different C8 products.

Bioinspired aerobic oxidation of alcohols with a bifunctional ligand based on bipyridine and TEMPO

A novel bioinspired bifunctional ligand incorporating metal-binding site and stable free radical has been synthesized. The catalytic system obtained from the bifunctional ligand with copper(i) iodide in the presence of N-methylimidazole is highly efficient for the oxidation of a broad range of primary benzylic, allylic, alkynyl, aliphatic alcohols and secondary benzylic alcohols to the corresponding aldehydes and ketones in good to excellent yields. The catalyst system exhibits broad functional-group compatibility. The reaction is carried out in acetonitrile as solvent under air balloon at room temperature. The catalyst system features excellent activity for primary aliphatic alcohol oxidation and a high chemoselective oxidation of primary alcohols over the secondary alcohols. This oxidation process is readily amenable to larger-scale application. The interaction of the different components in the reaction mixtures was studied by UV-visible spectroscopy. The data indicated that Cu(i) existed throughout the reaction. A plausible mechanism of the catalytic cycle is proposed.

Highly efficient oxidation of alcohols catalyzed by a porphyrin-inspired manganese complex

A novel strategy for catalytic oxidation of a variety of benzylic, allylic, propargylic, and aliphatic alcohols to the corresponding aldehydes or ketones by an in situ formed porphyrin-inspired manganese complex in excellent yields (up to 99%) has been successfully developed.

Cross aldol condensation of acetaldehyde and formaldehyde in the presence of bifunctional systems

Liquid-phase cross-aldol condensation of acetaldehyde and formaldehyde in the presence of salts of various saturated and unsaturated linear amines, aromatic amines, diamines, and nitrogen bases, as well as in the presence of substituted piperazines, linear and cyclic amino acids and their derivatives, and nitrogen-containing ionic liquids, was studied. The cross-condensation products were formed in considerable amounts when amine hydrochlorides, N-benzoyl amino acids, and amino acid esters were used as catalyst. The formation of cross-condensation products is favored by increased basicity of the amino nitrogen atom in the salt and of the solvent.