Oxidation Reactions with Aliphatic Peracids

Greenspan, Frank P.

doi:10.1021/ie50451a011

Cited by 41 publications

(19 citation statements)

References 2 publications

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“…Contrary to the statements of Greenspan (9) and S w r n et al (21) to the efect that the liydroxj-acetoxj-compounds could be isolated in high \.ields using this procedure, the chief product isolated was identified as the dihl-droxy compound both bj-melting point and hydroxyl value.…”

Section: Peracetic Acid Oxidationcontrasting

confidence: 64%

“…The method of perforinic acid oxidatioil was essentially that of Greenspan (9). In the preparation of large batches of hj,drosylated rapeseed oil acids for the isolation of dihydroxybehenic acid by fractional crystallization, the following method was used: 200 gm.…”

Section: Performic Acid Oxidationmentioning

confidence: 99%

“…Performic acid oxidatioil of rapeseed oil triglycerides according to a modified procedure of Greenspan (9) was therefore investigatecl to determine ~vllether seine polymerization occurs during the hydroxylation.…”

Section: Introductionmentioning

confidence: 99%

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Hydroxylation and Epoxidation of Rapeseed Oil Derivatives With Subsequent Pyrolysis and Ammonolysis

Mageli¹,

Patteson²,

Spencer³

1953

Can. J. Chem.

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A method was developed to follow the hydroxylation of rapeseed oil and erucic acid derivatives with peracetic acid. Peracetic acid prepared insitu was found to be equally as effective as the preformed acid in hydroxylation of methyl erucate. Among the compounds synthesized were ethyl 13,14-dihydroxybehenate, methyl 13,14-oxidoerucate, ethyl 13,14-diacetoxybehenate, and methyl 13,14(14,13)-hydroxyacetoxybehenate which were subsequently pyrolyzed at approximately 300 °C with p-toluenesulphonic acid as catalyst. The first compound yielded mainly the corresponding ketone with a small amount of the oxido derivative, the chief product of the second compound was also the ketone with some unsaturated material, the third compound yielded 43% of the diene, while the last one yielded 60%. Ammonolysis of the oxido compound or the bromohydrin to yield the corresponding aminohydroxy derivative under pressure with liquid ammonia and ammonium bromide was unsuccessful. A new compound oxidoerucamide, m.p.101.5°, was synthesized.

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Section: Peracetic Acid Oxidationcontrasting

confidence: 64%

Section: Performic Acid Oxidationmentioning

confidence: 99%

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Hydroxylation and Epoxidation of Rapeseed Oil Derivatives With Subsequent Pyrolysis and Ammonolysis

Mageli¹,

Patteson²,

Spencer³

1953

Can. J. Chem.

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“…If m ‐CPBA was replaced with peracetic acid, no recycling of the co‐product (acetic acid in this case) was modeled because its isolation from the aqueous medium would require additional steps after extraction with ethyl acetate (Figure S3 in the Supporting Information). The synthesis of peracetic acid was modeled based on data from the literature . The use of peracetic acid instead of m ‐CPBA leads to a decrease of approximately 18 % of the GWP of the chemical synthesis (Figure b).…”

Section: Resultsmentioning

confidence: 99%

A Prospective Life Cycle Assessment (LCA) of Monomer Synthesis: Comparison of Biocatalytic and Oxidative Chemistry

et al. 2019

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Biotechnological processes are typically perceived to be greener than chemical processes. A life cycle assessment (LCA) was performed to compare the chemical and biochemical synthesis of lactones obtained by Baeyer–Villiger oxidation. The LCA is prospective (based on experiments at a small scale with primary data) because the process is at an early stage. The results show that the synthesis route has no significant effect on the climate change impact [(1.65±0.59) kgCO2 gproduct−1 vs. (1.64±0.67) kgCO2 gproduct−1]. Key process performance metrics affecting the environmental impact were evaluated by performing a sensitivity analysis. Recycling of solvents and enzyme were shown to provide an advantage to the enzymatic synthesis. Additionally, the climate change impact was decreased by 71 % if renewable electricity was used. The study shows that comparative LCAs can be used to usefully support decisions at an early stage of process development.

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“…Peracetic acid used for the oxidation of the feather was prepared by the method of Greenspan (1947), modified for the use of 30% hydro gen peroxide. The pH of the peracetic acid was adjusted in the cold to 4.5 by the addition of concentrated sodium hydroxide.…”

Section: Feather Keratin Fibrilsmentioning

confidence: 99%

Cross [beta] structure in fibrils of feather keratin and of insulin

Burke

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Oxidation Reactions with Aliphatic Peracids

Cited by 41 publications

References 2 publications

Hydroxylation and Epoxidation of Rapeseed Oil Derivatives With Subsequent Pyrolysis and Ammonolysis

Hydroxylation and Epoxidation of Rapeseed Oil Derivatives With Subsequent Pyrolysis and Ammonolysis

A Prospective Life Cycle Assessment (LCA) of Monomer Synthesis: Comparison of Biocatalytic and Oxidative Chemistry

Cross [beta] structure in fibrils of feather keratin and of insulin

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