135689-01-9

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 67-64-1 acetone 
• 4023-79-4 1-(4-methylphenyl)butan-1,3-dione 
• 122-00-9 para-methylacetophenone 
• 24165-63-7 1-p-tolyl-3-buten-1-ol 

Downstream Products

• 1204698-96-3 (1R,3R)-1-(4-methylphenyl)-1,3-butandiol 
• 1204698-95-2 (1S,3R)-1-(4-methylphenyl)-1,3-butandiol 
• 3160-38-1 (E)-4-p-tolylbut-3-en-2-one 

Relevant academic research and scientific papers

Biomass waste-derived recyclable heterogeneous catalyst for aqueous aldol reaction and depolymerization of PET waste

In this work, we discuss the valorization of biomass waste-derived orange peel ash (OPA) by exploring its applicability as a heterogeneous catalyst in aqueous aldol reactions and demonstrating its versatility by promoting the methanolysis of poly(ethylene terephthalate) (PET) waste. The catalyst was characterized using Fourier-transform infrared spectroscopy (FT-IR), Brunauer-Emmett-Teller (BET) analysis, X-ray powder diffraction (XRD), X-ray fluorescence (XRF), energy dispersive X-ray (EDX) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), and thermal gravimetric analysis (TGA) to decode its chemical composition. The aldol reactions were carried out at ambient temperature in the presence of water as a solvent. PET depolymerization was performed in an autoclave for 1 h using only 6% w/w OPA. The catalyst was recovered and reused in both the reactions for up to four successive cycles with minimal loss in the catalytic activity. The use of OPA as a cost-free, eco-friendly and effective recyclable catalyst enables a greener route for C-C bond formation and PET waste recycling.

MnO2as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins

Efficient and mild reaction conditions for Wacker-type oxidation of terminal olefins of less explored homoallyl alcohols to β-hydroxy-methyl ketones have been developed by using a Pd(ii) catalyst and MnO2 as a co-oxidant. The method involves mild reaction conditions and shows good functional group compatibility along with high regio- and chemoselectivity. While our earlier system of PdCl2/CrO3/HCl produced α,β-unsaturated ketones from homoallyl alcohols, the present method provided orthogonally the β-hydroxy-methyl ketones. No overoxidation or elimination of benzylic and/or β-hydroxy groups was observed. The method could be extended to the oxidation of simple terminal olefins as well, to methyl ketones, displaying its versatility. An application to the regioselective synthesis of gingerol is demonstrated.

Interfacial Control of Catalytic Activity in the Aldol Condensation: Combining the Effects of Hydrophobic Environments and Water

Aminopropyl-functionalized mesoporous silica nanoparticles (AP-MSN) catalyze aldol condensations. The activity of AP-MSN decreases with increasing solvent polarity due to the stabilization of ion pairs formed between acidic silanol groups and the amines, which ultimately decreases the number of catalytically active amine sites. However, the reaction in water is faster than expected on the basis of polarity, because water limits the formation of Schiff bases that are also responsible for blocking active sites. In this work, we combined the action of water with a low-local-polarity environment around the catalytic sites of AP-MSN to maximize active site availability and catalyst performance. We specifically demonstrate how the local polarity of AP-MSN can be controlled by modifying its surface with varying concentrations of hexyl groups and how the dielectric constant of the silica-water interface can be determined using the solvatochromic probe Prodan. The catalytic activities of hexyl-modified AP-MSN in water were inversely proportional to their interfacial dielectric constants and were significantly higher (roughly by a factor of 4) than those of AP-MSN in anhydrous solvents of comparable polarities. Producing low-local-polarity environments in aqueous AP-MSN also enhanced the sensitivity of the aldol reaction to the electronic effects of substituents in the substrate. The enhancement of catalytic activity by low interfacial polarity was also observed in other amine-catalyzed C-C bond forming reactions such as the Henry and vinylogous aldol reactions. Overall, our results demonstrate that the catalytic activity of AP-MSN can be controlled by the synergistic action of water and a low interfacial dielectric constant.

Traceless OH-Directed Wacker Oxidation-Elimination, an Alternative to Wittig Olefination/Aldol Condensation: One-Pot Synthesis of α,β-Unsaturated and Nonconjugated Ketones from Homoallyl Alcohols

A new method for one-pot synthesis of β-substituted and β,β-disubstituted α,β-unsaturated methyl ketones from homoallyl alcohols by sequential PdCl2/CrO3-promoted Wacker process followed by an acid-mediated dehydration reaction has been developed. Remarkably, internal homoallyl alcohols delivered regioselectively nonconjugated unsaturated carbonyl compounds under the same protocol. A new starting material-based synthesis of α,β-unsaturated and nonconjugated methyl ketones is demonstrated.

PH-Tuned modulation of 1d chain to 3d metal-organic framework: Synthesis, structure and their useful application in the heterogeneous claisen-Schmidt reaction

The role of pH in the formation of metal-organic frameworks (MOFs) has been studied on magnesium-based carboxylate framework systems [Mg(Pdc)(H2O)3]n (1) and [Mg(Pdc)(H2O)]n (2) (Pdc=pyridine-2,3-dica

Investigation of proline amides and pyridinium salts as catalyst for direct aldol reactions in water

The catalytic potential of chiral proline amides and pyridinium salts in the aldol condensation in water was investigated. The aldol reactions of acetone with various aromatic aldehydes were carried out in water by using proline amide derivatives and pyri

Aldol condensation in PEG-400 catalyzed by recyclable l-proline supported on nano gold surface

l-Proline supported on nano gold surface in PEG-400 catalyst system has been developed for use in the direct aldol condensation of acetone with aldehydes. Successful immobilization on surface of gold nanoparticles was confirmed using multiple analytical t

A magnesium-based multifunctional metal-organic framework: Synthesis, thermally induced structural variation, selective gas adsorption, photoluminescence and heterogeneous catalytic study

Three magnesium based carboxylate framework systems were prepared through a temperature-dependent synthesis. The compounds were synthesized by a hydrothermal method and characterized by single crystal X-ray diffraction analysis. A stepwise increase in the

Substituent-dependent reactivity in aldehyde transformations: 4-(phenylethynyl)benzaldehydes versus simple benzaldehydes

Effects of substituents on transformations of 4-(phenylethynyl) benzaldehydes and related benzaldehydes were analyzed in aldol and thiazolidine formation reactions. The aldol reaction of 4-cyanobenzaldehyde was 54-fold faster than that of 4-methoxybenzald

Barium carboxylate metal-organic framework - Synthesis, x-ray crystal structure, photoluminescence and catalytic study

A new 3D alkaline earth metal-organic framework (MOF), [Ba(Hdcp)H 2O]n (1) (H3dcp = 3,5-pyrazoledicarboxylic acid), has been hydrothermally synthesized and structurally characterized by single-crystal X-ray diffraction ana