Reactions of Ozonides. IX. A Radioisotopic Dilution Study of Ozonide Methanolysis

Kerur, Dundappa R.; Diaper, D. G. M.

doi:10.1139/v72-636

Cited by 7 publications

(1 citation statement)

References 6 publications

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“…The formation of hydroperoxides, 4 especially in protic solvents such as methanol, 4 cannot be ruled out but was not considered herein in light of the fact that ozonolysis of various olefins, especially highly substituted olefins, in methanol still furnished the SOZ as a major product. Indeed, the high stabilities of SOZ in methanol 5 and THF 6 have been reported even at the reflux temperatures of each solvent.…”

Section: Introductionmentioning

confidence: 99%

The Development of Continuous Process for Alkene Ozonolysis Based on Combined in Situ FTIR, Calorimetry, and Computational Chemistry

Allian

Richter

Kallemeyn

et al. 2010

Org. Process Res. Dev.

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Two continuous apparatuses were designed that are capable of safely scaling the highly energetic ozonolysis reaction to multikilogram scale where flow chemistry allowed excellent temperature control and minimized the inventory of the highly unstable ozonide intermediate. First, a continuous stirred tank reactor was developed and proven capable of generating product at a rate of 77 mmol of product per hour while maintaing <46 mmol of ozonide. Then, a larger-scale continuous bubble reactor was designed to deliver 770 mmol of product per hour while maintaing 950 mmol of ozonide present at any given time, and the latter was utilized to deliver 2.5 kg of product. The development of these reactors relied on careful evaluation of the thermal stability and heat of reaction of ozonolysis using computational chemistry and calorimetric measurement. In addition, the reactor design benefited from in situ ATR/FTIR monitoring of the rate of ozonolysis under nonflow conditions which allowed for the flow of substrate to be matched with ozone generation, enabling complete reaction of the alkene with minimal excess of ozone.

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Section: Introductionmentioning

confidence: 99%

The Development of Continuous Process for Alkene Ozonolysis Based on Combined in Situ FTIR, Calorimetry, and Computational Chemistry

Allian

Richter

Kallemeyn

et al. 2010

Org. Process Res. Dev.

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: RK. VON OZONIDEN 9. MITT. RADIOISOTOPEN‐VERDUENNUNGS‐UNTERSUCHUNG DER OZONID‐METHANOLYSE

Kerur¹,

Diaper²

1973

Chemischer Informationsdienst

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Benzylidene fluorene ozonolysis under chemiluminescence mimetic conditions in homegeneous and micellar media I: Kinetic law as a function of hammett's σ constants and quenching by the leaving moiety

Papalambros

Nikokavouras

1987

Journal of Photochemistry

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Reactions of Ozonides. IX. A Radioisotopic Dilution Study of Ozonide Methanolysis

Abstract: A radioisotopic dilution study indicates that no significant amounts of[Formula: see text]are produced by reacting [Formula: see text] with methanol.

Cited by 7 publications

References 6 publications

The Development of Continuous Process for Alkene Ozonolysis Based on Combined in Situ FTIR, Calorimetry, and Computational Chemistry

The Development of Continuous Process for Alkene Ozonolysis Based on Combined in Situ FTIR, Calorimetry, and Computational Chemistry

ChemInform Abstract: RK. VON OZONIDEN 9. MITT. RADIOISOTOPEN‐VERDUENNUNGS‐UNTERSUCHUNG DER OZONID‐METHANOLYSE

Benzylidene fluorene ozonolysis under chemiluminescence mimetic conditions in homegeneous and micellar media I: Kinetic law as a function of hammett's σ constants and quenching by the leaving moiety

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