94992-76-4

Upstream product

• 928-95-0 (E)-2-Hexen-1-ol 

Downstream Products

• 76741-12-3 (2S,3R)-3-methylhexane-1,2-diol 
• 76741-13-4 (2R,3S)-3-methylhexane-1,2-diol 
• 110918-65-5 (2'S,3'R)-2',3'-epoxyhexyl 3,5-dinitrobenzoate 
• 142129-25-7 (-)-2--(2S,3R)-3-propyloxirane 
• 169738-71-0 (+)-2-<(phenylthio)methyl>-(2R,3R)-3-propyloxirane 
• 693220-90-5 (2R,3S)-3-(3,5-dichloro-phenoxy)-hexane-1,2-diol 
• 1609086-78-3 C₁₂H₁₈O₃ 
• 110918-75-7 (2R,3R,4S)-2,4-dimethyl-3-tetrahydropyranyloxyheptyl tosylate 
• 188883-02-5 Dibenzyl-((2S,3R)-3-propyl-oxiranylmethyl)-amine 

Relevant academic research and scientific papers

Pore size matters! Helical heterogeneous catalysts in olefin oxidation

Helical mesoporous materials of the MCM-41 type with different pore sizes were prepared, choosing as templates myristyl (C14) or cetyl (C16) trimethyl ammonium salts, and functionalized with Mo(II) active sites based on MoI2(CO)3 (1) and MoBr(η3-C3H5)(CO)2 (2) fragments, respectively, using a pyridine-2-carbaldehyde ligand as anchor. The new materials were tested as the catalytic precursors in the epoxidation of cis-cyclooctene, styrene, R-(+)-limonene, trans-hex-2-en-1-ol, cis-3-hex-1-ol, and geraniol using tert-butylhydroperoxide (tbhp) as oxidant. All catalysts were moderately to highly selective toward the epoxide products. The materials with larger pores (C16 template) displayed a better catalytic activity, leading in general to higher conversions and selectivities, as well as faster kinetics. For instance, geraniol is epoxidized (more than 90%) with conversions above 90%. The major achievement of these catalysts, however, is the excellent product selectivity control, which is boosted when the allyl complex 1 is used, reaching 100% of the 2S, 3R species in the epoxidation of trans-hex-2-en-1-ol. The catalysts were also found to be stable through recycling experiments and truly heterogeneous with little or no leaching.

Process for cooxidizing organic compounds, process for producing epoxy compounds and process for producing esters or lactones

According to the inventive co-oxidation process of organic compounds, (A) a compound selected from (A1) a compound having a non-aromatic ethylenic bond and (A2) a ketone or an alcohol corresponding to the ketone is oxidized by molecular oxygen in the presence of N-hydroxyphthalimide or another imide compound and in the coexistence of (B) a compound oxidizable by the imide compound and oxygen and different from the compound (A). As the compound (B), (a) primary or secondary alcohols (e.g., benzhydrol, cyclohexanol), (b) compounds each having a carbon-hydrogen bond at the adjacent position to an unsaturated bond (e.g., tetralin, ethylbenzene) and the like can be used. According to this process, a corresponding epoxy compound from the compound (A1) having a non-aromatic ethylenic bond, and a corresponding ester or lactone from the ketone or its corresponding alcohol (A2) can be obtained in satisfactory yields.

Mechanism of asymmetric epoxidation. 1. Kinetics

The rate of titanium-tartrate-catalyzed asymmetric epoxidation of allylic alcohols is shown to be first order in substrate and oxidant, and inverse second order in inhibitor alcohol, under pseudo-first-order conditions in catalyst. The rate is slowed by substitution of electron-withdrawing substituents on the olefin and varies slightly with solvent, CH2Cl2 being the solvent of choice. Asymmetric induction suffers when the size of the alkyl hydroperoxide is reduced. Kinetic resolution of secondary allylic alcohols is shown to be sensitive to the size of the tartrate ester group and insensitive to the steric nature of inhibitor alcohol. Most importantly, the species containing equimolar amounts of Ti and tartrate is shown to be the most active catalyst in the reaction mixture, mediating reaction at much faster rates than titanium tetraalkoxide alone.