10275-88-4

Upstream product

• 10276-21-8 isophorone oxide 
• 308358-04-5 (6R)-2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-one 
• 109-63-7 trifluoroborane diethyl ether 
• 71-43-2 benzene 

Downstream Products

• 4694-12-6 2,4,4-trimethylcyclopentan-1-one 
• 603944-69-0 6,6,7a-trimethyl-5,6,7,7a-tetrahydrocyclopenta[c]pyran-3(1H)-one 
• 588718-93-8 2-hydroxymethyl-2,4,4-trimethylcyclopentanol 
• 104461-82-7 2-hydroxymethyl-2,4,4-trimethylcyclopentanone 
• 588718-93-8 2-hydroxymethyl-2,4,4-trimethylcyclopentanol 

Relevant academic research and scientific papers

Niobium pentachloride catalysed ring opening of epoxides

Epoxide ring opening is a frequently required transformation in Organic Synthesis. In this paper we describe the application of NbCl5 for this purpose using three different substrates. Chlorohydrins, 1,2-diols, products containing solvent resid

Nanocrystalline ZSM-5: A catalyst with high activity and selectivity for epoxide rearrangement reactions

Nanocrystalline ZSM-5 (～20-50 nm) has been tested as a catalyst in the liquid phase rearrangement of 1,2-epoxyoctane, 2-methyl-2,3-epoxybutane and isophorone oxide together with a microcrystalline ZSM-5 sample (～5 μm) employed as a reference. Whereas this last material shows a low activity for the three epoxide rearrangement reactions considered, nanocrystalline ZSM-5 leads in all cases to high epoxide conversion. This different catalytic performance is attributed to the differences in the accessibility of the reactant molecules to the catalyst active sites. The smallest crystal size of the nanocrystalline zeolite contributes favourably to both the formation of a high external surface area, with no steric constraints, and to a faster intracrystalline diffusion of the epoxide molecules towards the acid sites located within the zeolite micropores. When sterically hindered epoxides are tested, the catalytic rearrangement occurs mainly on the external surface of the nanocrystalline zeolite. Moreover, it is remarkable that for the three epoxides investigated the high catalytic activity observed over nanocrystalline ZSM-5 is accompanied by the attainment of high selectivities, typically around or over 80%, towards products with commercial applications.

Opening of epoxide rings catalyzed by niobium pentachloride

The behavior of several epoxides when treated with NbCl5 was studied. In general, the studied epoxides reacted rapidly with NbCl5, giving, in most cases, more than one product (chlorohydrins, products containing solvent residues, as well as rearrangement products). A detailed study was performed to verify the effects of the temperature (rt, 0°C, or -78°C) and of the NbCl5 molar concentration on the composition of the products, yield, and time required for the reactions. Copyright Taylor & Francis Group, LLC.

Solid-acid catalysed rearrangement of cyclic α,β-epoxy ketones

Various cyclic α,β-epoxy ketones rearranged to α-formyl ketones and/or vicdiones in the presence of catalytic amounts of zeolites and montmorillonite K10. This provides an excellent alternative to conventional homogeneous systems with respect to yields and workup. Differences in product distribution and type of products in the rearrangement of pulegone oxide could be reasonably explained by invoking different pathways for homogeneous and heterogeneous catalysts.