Synthesis of carvacrol by Friedel–Crafts alkylation of <i>o</i>‐cresol with isopropanol using superacidic catalyst UDCaT‐5

Yadav, Ganapati D.; Kamble, Shashikant B.

doi:10.1002/jctb.2210

Cited by 32 publications

(20 citation statements)

References 25 publications

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“…The drastic decrease in the overall ether selectivity at high conversion is most likely due to the fast ether decomposition mentioned above. However, for a given conversion level, this selectivity increases with the isopropanol/m‐cresol ratio, in agreement with the trends reported for the alkylation of m‐cresol and o‐cresol with isopropanol and tert ‐butanol . As shown in Figure , using propylene as alkylating agent instead of isopropanol, at the same C3/m‐cresol ratio and same level of conversion, results in a much lower selectivity toward ethers.…”

Section: Resultssupporting

confidence: 88%

“…Accordingly, the first step is the dehydration of the alcohol. From our experiments and previous studies, it was observed that dehydration of isopropanol can occur via two parallel paths, one is the direct dehydration and the other via formation of di‐isopropyl ether, which can further decompose to propylene and water

Isopropanol \to Propylene + Water

Isopropanol \to Di - isopropyl ether + Water

Di - isopropyl ether \to Propylene + Water

…”

Section: Resultssupporting

confidence: 59%

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Reaction pathways in the liquid phase alkylation of biomass‐derived phenolic compounds

González-Borja

Resasco

2014

AIChE Journal

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Alkylation is a promising reaction for the upgrading of bio-oil because it maximizes the retention of carbon in the liquid product. The alkylation of m-cresol with isopropanol and HY zeolite was studied in a liquid phase system. The experimental results were fitted with two conventional surface kinetic models, Langmuir-Hinshelwood and Eley-Rideal, from which adsorption and rate constants were estimated. Two types of alkylation reactions were observed: C-alkylation with formation of a CAC bond with the ring and O-alkylation with formation of an ether bond with the hydroxyl group. It was concluded that O-alkylation products do not undergo intramolecular rearrangement but first decompose into the corresponding phenolic. Alkylation occurs from both isopropanol and propylene, both of them yielding O-and C-alkylation to different extents. Isopropanol favors O-alkylation while propylene favors C-alkylation. Rate constants for multiple alkylation steps were progressively lower, suggesting the presence of steric hindrance during incorporation of additional isopropyl groups.

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Section: Resultssupporting

confidence: 88%

Isopropanol \to Propylene + Water

Isopropanol \to Di - isopropyl ether + Water

Di - isopropyl ether \to Propylene + Water

…”

Section: Resultssupporting

confidence: 59%

Reaction pathways in the liquid phase alkylation of biomass‐derived phenolic compounds

González-Borja

Resasco

2014

AIChE Journal

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“…bergamia Loisel), and other plants (Fachini‐Queiroz et al, ; Kintzios, ; Lisin, Safiyev, & Craker, ; Tang, Chen, & Wang, ). Commercial CV is synthesized by chemical and biotechnological methods (Yadav & Kamble, ). It is also named 5‐isopropyl‐2‐methylphenol by the International Union of Pure and Applied Chemistry.…”

Section: Introductionmentioning

confidence: 99%

“…It is also named 5‐isopropyl‐2‐methylphenol by the International Union of Pure and Applied Chemistry. Carvacrol has lipophilic properties and a density of 0.976 g/ml at room temperature (25 °C); it is insoluble in water but highly soluble in ethanol, acetone, and diethyl ether (Yadav & Kamble, ). As recently reviewed by several authors (Baser, ; Suntres, Coccimiglio, & Alipour, ), this compound possesses a wide range of biological activities, including antibacterial and antifungal (Chavan & Tupe, ; Du et al, ; Nostro et al, ), antiviral (Gilling, Kitajima, Torrey, & Bright, ; Sánchez, Aznar, & Sánchez, ), antioxidant (Aristatile, Al‐Numair, Al‐Assaf, & Pugalendi, ; Guimarães et al, ; Milos & Makota, ), and anticarcinogenic properties (Arunasree, ; Ozkan & Erdogan, ; Q. H. Yin et al, ; Figure ).…”

Section: Introductionmentioning

confidence: 99%

Carvacrol and human health: A comprehensive review

Sharifi‐Rad

Varoni

Iriti

et al. 2018

Phytotherapy Research

410

261

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Carvacrol (CV) is a phenolic monoterpenoid found in essential oils of oregano (Origanum vulgare), thyme (Thymus vulgaris), pepperwort (Lepidium flavum), wild bergamot (Citrus aurantium bergamia), and other plants. Carvacrol possesses a wide range of bioactivities putatively useful for clinical applications such antimicrobial, antioxidant, and anticancer activities. Carvacrol antimicrobial activity is higher than that of other volatile compounds present in essential oils due to the presence of the free hydroxyl group, hydrophobicity, and the phenol moiety. The present review illustrates the state-of-the-art studies on the antimicrobial, antioxidant, and anticancer properties of CV. It is particularly effective against food-borne pathogens, including Escherichia coli, Salmonella, and Bacillus cereus. Carvacrol has high antioxidant activity and has been successfully used, mainly associated with thymol, as dietary phytoadditive to improve animal antioxidant status. The anticancer properties of CV have been reported in preclinical models of breast, liver, and lung carcinomas, acting on proapoptotic processes. Besides the interesting properties of CV and the toxicological profile becoming definite, to date, human trials on CV are still lacking, and this largely impedes any conclusions of clinical relevance.

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“…Carvacrol is highly lipophilic; the solubility of carvacrol is very high in carbon tetrachloride, ethanol, diethyl ether, acetone; but insoluble in water (Ultee et al, 2000). Yadav and Kamble (2009) reported that formation of carvacrol could be resulted from alkylation of o-cresol with propylene or isopropyl alcohol (IPA) over solid acid catalysts.…”

Section: Chemical and Physical Characteristicsmentioning

confidence: 99%

Biological Effects and Modes of Action of Carvacrol in Animal and Poultry Production and Health - A Review

Alagawany¹

2015

Adv. Anim. Vet. Sci.

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The carvacrol compound is an antioxidant nutrient, used to enhance growth and productive performance via modification and activation of gastrointestinal tract structure and function and to inhibit/prevent cancer initiations. Numerous studies performed on animal diets supplemented with phytogenic supplements/feed additives containing natural antioxidants such as carvacrol demonstrated its capability to improve performance indices, feed utilization, immune functions and health of livestock as well as reducing the risks of different animal diseases like cancer and other diseases. Such properties could be due to its ability as antimicrobial, antioxidant, antifungal, immunomodulatory, anticancer and anti-inflammatory agents by preventing free radicals and hazardous compounds from interacting with cellular DNA and its ability to change the gut microflora, improving digestion coefficient and absorption of nutrient compounds. The present review illustrates the chemical and physical proprieties, modes of action, metabolism and excretion, biological properties, natural sources and beneficial aspects of carvacrol in animal and poultry production and health.

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Synthesis of carvacrol by Friedel–Crafts alkylation of o‐cresol with isopropanol using superacidic catalyst UDCaT‐5

Abstract: BACKGROUND: Alkylation of o-cresol with propylene or isopropyl alcohol (IPA) over solid acid catalysts results in the formation of carvacrol, which finds potential applications in the synthesis of fine chemicals, intermediates, specialty chemicals, flavours and fragrances.

Cited by 32 publications

References 25 publications

Reaction pathways in the liquid phase alkylation of biomass‐derived phenolic compounds

Reaction pathways in the liquid phase alkylation of biomass‐derived phenolic compounds

Carvacrol and human health: A comprehensive review

Biological Effects and Modes of Action of Carvacrol in Animal and Poultry Production and Health - A Review

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