Transformation of α-limonene into p-cymene over oxide catalysts: A green chemistry approach

Kamitsou, Maria D.; Panagiotou, George D.; Triantafyllidis, Konstantinos S.; Bourikas, Kyriakos; Lycourghiotis, Alexis; Kordulis, Christos

doi:10.1016/j.apcata.2013.06.001

Cited by 41 publications

(39 citation statements)

References 32 publications

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“…Due to industrial interest in p-cymene in the synthesis of pesticides, fungicides, perfumes, fragrances and as a starting material for the synthesis of p-cresol, which is in turn used in the production of antioxidants like butylated hydroxytoluene (BHT) [ 42 ], the synthesis of p-cymene has been the target of several studies. According to Kamitsou et al (2014) [ 43 ], p-cymene is conventionally produced by the Friedel-Crafts alkylation of toluene with isopropanol, or of benzene with methyl or isopropyl halides. The catalysts of these reactions are generally solutions of HCl acid with AlCl 3 , BF 3 or H 2 SO 4 .…”

Section: Bioavailability and Synthesismentioning

confidence: 99%

Update on Monoterpenes as Antimicrobial Agents: A Particular Focus on p-Cymene

et al. 2017

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p-Cymene [1-methyl-4-(1-methylethyl)-benzene] is a monoterpene found in over 100 plant species used for medicine and food purposes. It shows a range of biological activity including antioxidant, anti-inflammatory, antinociceptive, anxiolytic, anticancer and antimicrobial effects. This last property has been widely investigated due to the urgent need for new substances with antimicrobial properties, to be used to treat communicable diseases whose diffusion in developed countries has been facilitated by globalization and the evolution of antimicrobial resistance. This review summarizes available scientific data, as reported by the most recent studies describing the antimicrobial activity of p-cymene either alone, or as the main component of plant extracts, as well as addressing the mechanisms of action of cymenes as antimicrobial agents. While p-cymene is one of the major constituents of extracts and essential oils used in traditional medicines as antimicrobial agents, but considering the limited data on its in vivo efficacy and safety, further studies are required to reach a definitive recommendation on the use and beneficial effects of p-cymene in human healthcare and in biomedical applications as a promising candidate to functionalize biomaterials and nanomaterials.

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Section: Bioavailability and Synthesismentioning

confidence: 99%

Update on Monoterpenes as Antimicrobial Agents: A Particular Focus on p-Cymene

et al. 2017

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“…p-Cymene is a readily available aromatic compound that can be derived from pine resin or prepared by dehydrogenation of a-pinene, bpinene, and limonene. [15][16][17][18][19] Recent reports have also shown that p-cymene can be obtained by deoxygenation of terpenoid ethers. 20,21 Other researchers have shown that several of these terpene feedstocks and p-cymene itself can be prepared biosynthetically from biomass sugars.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of a high temperature thermosetting polyimide oligomer derived from a non-toxic, sustainable bisaniline

et al. 2017

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“…Several methods have been developed for the polymerization of cyclic terpenes, specifically α‐pinene, β‐pinene, and limonene, via cationic, radical, or ring‐opening metathesis polymerization of carbon–carbon double bonds . 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 .…”

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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Transformation of α-limonene into p-cymene over oxide catalysts: A green chemistry approach

Cited by 41 publications

References 32 publications

Update on Monoterpenes as Antimicrobial Agents: A Particular Focus on p-Cymene

Update on Monoterpenes as Antimicrobial Agents: A Particular Focus on p-Cymene

Synthesis and characterization of a high temperature thermosetting polyimide oligomer derived from a non-toxic, sustainable bisaniline

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

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