Organocatalyzed Epoxidation of Alkenes in Continuous Flow using a Multi‐Jet Oscillating Disk Reactor

Spaccini, Raffaele; Liguori, Lucia; Punta, Carlo; Bjørsvik, Hans‐René

doi:10.1002/cssc.201100262

Cited by 36 publications

(18 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…This protocol was successfully applied on a larger scale (1 liter Büchi glass vessel) for the synthesis of propylene oxide from the corresponding propene [56], and more recently under continuous-flow conditions, by means of a new multijet oscillating disk (MJOD) reactor, designed and developed by Bjørsvik and co-workers [57]. In this latter case we succeeded in accelerating the overall process, shortening the residence time with respect to the batch protocol.…”

Section: Reviewmentioning

confidence: 99%

Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review

Melone¹,

Punta²

2013

Beilstein J. Org. Chem.

Self Cite

151

View full text Add to dashboard Cite

SummarySince the beginning of the century, N-hydroxyphthalimide and related compounds have been revealed to be efficient organocatalysts for free-radical processes and have found ample application in promoting the aerobic oxidation of a wide range of organic substrates. When combined with different co-catalysts, they are activated to the corresponding N-oxyl radical species and become able to promote radical chains, involving molecular oxygen, directly or indirectly. Most of the examples reported in the literature describe the use of these N-hydroxy derivatives in the presence of transition-metal complexes. However, eco-friendly standards, including the demand for highly selective transformations, impose the development of metal-free processes, especially for large-scale productions, as in the case of the oxygenation of hydrocarbons. For this reason, many efforts have been devoted in the past decade to the design of new protocols for the activation of N-hydroxy imides in the presence of nonmetal initiators. Herein we provide a concise overview of the most significant and successful examples in this field, with the final aim to furnish a useful instrument for all scientists actively involved in the O2-mediated selective oxidation of organic compounds and looking for environmentally safe alternatives to metal catalysis.

show abstract

Section: Reviewmentioning

confidence: 99%

Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review

Melone¹,

Punta²

2013

Beilstein J. Org. Chem.

Self Cite

151

View full text Add to dashboard Cite

show abstract

“…[18,19] Aldehydes may generate PINO radicals, even at room temperature, through the formation of the corresponding peracetic acid under an oxygen atmosphere and consequent molecule-induced homolysis with 1 (Scheme 3). [37][38][39] In line with our previous works, we decided to perform the oxidation of CU, EtB, and CHB by using propionaldehyde as the initiator and comparing the performances of 1 and 3 at 70 8C. In the case of CU and CHB (Table 5, entries 1-4 and 5-6), we worked with a HC/ACN ratio (2.67:1) close to the solubility limits of 1 % 1.…”

Section: Aerobic Oxidation Of Alkylaromaticsmentioning

confidence: 95%

Aerobic Oxidation of Alkylaromatics using a Lipophilic N‐Hydroxyphthalimide: Overcoming the Industrial Limit of Catalyst Solubility

et al. 2014

Self Cite

View full text Add to dashboard Cite

4,4'-(4,4'-Isopropylidenediphenoxy)bis(N-hydroxyphthalimide), which is a new lipophilic analogue of N-hydroxyphthalimide, can act as an effective catalyst in the aerobic oxidation of alkylaromatics under reduced amounts of polar cosolvent. The catalyst was selected on the basis of an in-depth study of the influence that substituents on the aromatic ring of N-hydroxyphthalimide exert on determining the NO-H bond dissociation energy (BDE). BDE values for a range of model molecules are calculated by DFT and measured by EPR spectroscopy. The new catalyst can be successfully employed in the aerobic oxidation of cumene, ethylbenzene, and cyclohexylbenzene, affording, in all cases, good conversions and high selectivity for the corresponding hydroperoxide. The effect of solvent, catalyst, and temperature has also been investigated.

show abstract

“…For this reason, in 2012 we started a collaboration for realizing an aerobic epoxidation catalyzed by NHPI under continuous-flow conditions by means of a new technology designed, manufactured, and developed by prof. Biørsvik (University of Bergen) and Fluens Synthesis Company: the multijet oscillating disk (MJOD) reactor [14]. A flowchart of this reactor applied to the our process is reported in Fig.…”

Section: Epoxidation Of Olefinsmentioning

confidence: 99%

N ‐Hydroxyphthalimide (NHPI)‐Organocatalyzed Aerobic Oxidations: Advantages, Limits, and Industrial Perspectives

Melone

Punta

2016

Liquid Phase Aerobic Oxidation Catalysis: Industrial Applications and Academic Perspectives

Self Cite

View full text Add to dashboard Cite

Organocatalyzed Epoxidation of Alkenes in Continuous Flow using a Multi‐Jet Oscillating Disk Reactor

Cited by 36 publications

References 41 publications

Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review

Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review

Aerobic Oxidation of Alkylaromatics using a Lipophilic N‐Hydroxyphthalimide: Overcoming the Industrial Limit of Catalyst Solubility

N ‐Hydroxyphthalimide (NHPI)‐Organocatalyzed Aerobic Oxidations: Advantages, Limits, and Industrial Perspectives

Contact Info

Product

Resources

About