Conversion of d-Limonene to l-Carvone<sup>1</sup>

Royals, E. Earl; Horne, Samuel E.

doi:10.1021/ja01156a119

Cited by 49 publications

(19 citation statements)

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“…Maybe some traces are formed, however the results of analysis are ambiguous. The product profiles after 24 ] solv small amounts of oxidation products were observed. The results presented in Table 1 indicate that: (a) the use of bipyridine complexes of iron gives much better yields than aqua/solvent complexes, (b) there is no substantial difference in yields using Fe(II) or Fe(III) complexes, (c) the increase of the reaction yield is proportional to the increase of substrate concentration, (d) the products yield is proportional to the catalyst concentration in its low concentrations region, and (e) the use of air instead of dioxygen causes the decrease of the reaction yield approximately three times.…”

Section: Methodsmentioning

confidence: 99%

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Iron(II, III)-Catalyzed Oxidation of Limonene by Dioxygen

2007

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Labile iron(II) and iron(III) complexes {[Fe II (bpy) 2 2+ ] solv and [Fe III (bpy) 2 3+] solv } in acetonitrile activate dioxygen for the oxidation of limonene to produce mainly carvone, carveol, limonene oxide, and perillaldehyde. Iron(III) complex is reduced by the substrate to iron(II) one, which activates dioxygen. Probably the catalyst interacts with substrate prior to the oxidation process. Perillaldehyde is likely formed directly from oxidation of methyl group (not via alcohol). However, the aldehyde is also reduced to perillyl alcohol by the reduced form of the catalyst.

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Section: Methodsmentioning

confidence: 99%

“…The first starts with the reaction of limonene with nitrosyl chloride. The resulting nitrosochloride is then dehydrochlorinated to carvone oxime, which is hydrolyzed to L-carvone [23,24]. The other one involves the formation of the epoxide with peracetic acid, its hydrolysis to limonene glycol, which is oxidized by chromate [25,26].…”

Section: Introductionmentioning

confidence: 99%

Iron(II, III)-Catalyzed Oxidation of Limonene by Dioxygen

2007

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“…14,15 However, weak carboxylic acids, such as acetic acid or benzoic acid, require a strong acid catalyst for conversion to percarboxylic acid. 16,17 As alternatives to carboxylic acids, carboxylic anhydrides have been used for the in situ production of percarboxylic acid with H 2 O 2 . 18,19 Acetic anhydride, 20 triuoroacetic anhydride, 21,22 maleic anhydride, 23,24 and phthalic anhydride 25 have been used as mediators in oxidation reactions based on H 2 O 2 .…”

Section: Introductionmentioning

confidence: 99%

Recyclable anhydride catalyst for H₂O₂ oxidation: N-oxidation of pyridine derivatives

et al. 2020

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The catalytic efficiency and recyclability of poly(maleic anhydride-alt-1-octadecene) (Od-MA) and poly(maleic anhydride-alt-1-isobutylene) (Bu-MA) were evaluated for use in the development of a metalfree, reusable catalyst for the oxidation of pyridines to pyridine N-oxides in the presence of H 2 O 2 . The Od-MA catalyst was easily recovered via filtration with recovery yields exceeding 99.8%. The catalyst retained its activity after multiple uses and did not require any treatment for reuse. The Od-MA and H 2 O 2 catalytic system described herein is eco-friendly, operationally simple, and cost-effective; thus, it is industrially applicable. Od-MA and H 2 O 2 could potentially be used in place of percarboxylic acid as an oxidant in a wide range of oxidation reactions.

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“…However, few studies have focused on the development of polymers from p ‐cymene, an aromatic component of turpentine, which can also be readily synthesized by dehydrogenation of α‐pinene, β‐pinene, limonene, and other terpenes . A phenolic terpenoid, 2‐methyl‐5‐isopropylphenol (carvacrol), can be isolated from thyme and oregano essential oils or can be synthesized from a variety of turpentine components including p ‐cymene . A recent study by our laboratory demonstrated the conversion of carvacrol into a bisphenol that was subsequently used to make polycarbonates and a hydrophobic cyanate ester monomer .…”

Section: Introductionmentioning

confidence: 99%

Bio‐based hydrophobic epoxy‐amine networks derived from renewable terpenoids

Garrison

Harvey

2016

J of Applied Polymer Sci

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Carvacrol and p‐cymene are sustainable and versatile starting materials for the preparation of hydrophobic monomers. These molecules can be readily derived from pine resin or produced from other sustainable feedstocks via a biosynthetic approach. A hydrophobic epoxy monomer [bis(2‐isopropyl‐5‐methyl‐4‐(oxiran‐2‐ylmethoxy)phenyl)methane, 3] with methyl and isopropyl substituents on the aromatic rings was synthesized from carvacrol. A bisaniline [4,4′‐methylenebis(5‐isopropyl‐2‐methylaniline, 4] was then synthesized from p‐cymene. Using a cured epoxy‐amine network prepared from the diglycidyl ether of bisphenol A (DGEBA) and 4,4′‐methylenedianiline (MDA) as a baseline system, three additional networks were prepared from DGEBA:4, 3:MDA, and 3:4. The cured epoxy‐amine networks were tested for moisture uptake as well as changes in thermomechanical properties after exposure to boiling water for several days. Incorporation of the bio‐based monomers resulted in up to 53% lower water uptake compared to the baseline system. The bio‐based resins also showed greater resistance to degradation under hot‐wet conditions, with wet‐TG knockdowns as low as 8% as compared to a 19% decrease for the baseline system. These results show that the unique functionality of the renewable bisphenol and aniline used in this study can result in materials with improved hot/wet performance as compared to conventional thermosetting resins. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016, 133, 43621.

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Conversion of d-Limonene to l-Carvone¹

Cited by 49 publications

References 0 publications

Iron(II, III)-Catalyzed Oxidation of Limonene by Dioxygen

Iron(II, III)-Catalyzed Oxidation of Limonene by Dioxygen

Recyclable anhydride catalyst for H₂O₂ oxidation: N-oxidation of pyridine derivatives

Bio‐based hydrophobic epoxy‐amine networks derived from renewable terpenoids

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Conversion of d-Limonene to l-Carvone1

Cited by 49 publications

References 0 publications

Iron(II, III)-Catalyzed Oxidation of Limonene by Dioxygen

Iron(II, III)-Catalyzed Oxidation of Limonene by Dioxygen

Recyclable anhydride catalyst for H2O2 oxidation: N-oxidation of pyridine derivatives

Bio‐based hydrophobic epoxy‐amine networks derived from renewable terpenoids

Contact Info

Product

Resources

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Conversion of d-Limonene to l-Carvone¹

Recyclable anhydride catalyst for H₂O₂ oxidation: N-oxidation of pyridine derivatives