A bio-inspired heterogeneous catalyst for the transformation of limonene from orange peel waste biomass into value-added products

Becerra, Jaime-Andrés; González, Lina-María; Villa, Aída Luz

doi:10.1016/j.cattod.2017.07.012

Cited by 20 publications

(19 citation statements)

References 48 publications

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“…(1R)-(+)-Limonene (97%) and aqueous TBHP solution (70%) from Sigma-Aldrich and acetone (99.5%) from Merck, were used without further purification. The FePcCl16-NH2-SiO2 catalyst was synthesized according to the procedure reported in the literature [7]. The oxidation of limonene with TBHP was carried out in a batch reactor of 8 mL, 318 K, 750 rpm, 6 h, TBHP/limonene molar ratio of 2.6, with acetone as a solvent and 120 mg of FePcCl16-NH2-SiO2 (55.5 μmol Fe/g).…”

Section: 1catalyst Synthesis and Chemical Reactionsmentioning

confidence: 99%

“…After the reaction, the catalyst was removed and the GC-MS analysis of the resulting liquid sample showed as main components the solvent acetone, t-butanol from TBHP decomposition, the remaining unreacted reagents (limonene and TBHP), and the main monoterpene-derived reaction products (carvone, carveol and limonene 1,2-epoxide), among others terpenes [7], Table 1. Additionally, the large amount of water entering with the oxidizing agent remains almost constant during the reaction, since just small amounts can be obtained from the limonene transformation and secondary TBHP reactions [7]. The liquid reaction sample was fractionated by batch distillation and the separation was conducted under a cyclic total reflux policy with intermittent internal reflux ratio, i.e., varying r intermittently between 0 and 1.…”

Section: Experimental Evaluation Of Carvone Separationmentioning

confidence: 99%

“…Carvone is a cyclic ketone obtained from limonene oxidation with a high commercial cost (>10 USD kg -1 ) and is used in the synthesis of specialty chemical products for the food, pharmaceutical, agrochemical, and perfume industries [4][5][6]. However, from the oxidation of limonene with t-butyl hydroperoxide (TBHP) as the oxidizing agent and perchlorinated iron phthalocyanine on modified silica catalyst (FePcCl16-NH2-SiO2), Figure 1, other by-products such as limonene 1,2-epoxide and carveol are obtained (acetone, 313 K, 6 h, 750 rpm, TBHP/limonene = 2.6 mol/mol, 84 mg catalyst), with a limonene conversion of 76% and TBHP of 97%; additionally, t-butanol is obtained from the decomposition of TBHP [7]. Distillation is a physical separation process by selective evaporation and condensation of the components in a mixture regularly carried out continuously, in batch or semi-continuously, which results in a total or partial separation increasing the concentration of some components in the mixture due to the differences in volatility [8].…”

Section: Introductionmentioning

confidence: 99%

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Separation of carvone by batch distillation from the mixture obtained from limonene oxidation

Becerra

Villa

2021

Rev.Fac.Ing.Univ.Antioquia

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Limonene is the main constituent of citrus oils whose oxidation produces a set of fine chemical compounds such as carvone, carveol, and limonene 1,2-epoxide. This contribution reports the results of the experimental evaluation and computational simulation of carvone separation by fractional distillation from the reaction mixture. Carvone was obtained from limonene oxidation over a perchlorinated iron phthalocyanine supported on modified silica catalyst (FePcCl16-NH2-SiO2) and t-butyl hydroperoxide (TBHP) as oxidant. Both experimental and simulation results support that fractional distillation (in batch and continuous) is a suitable technique for concentrating carvone. However, in the presence of water, the formation of immiscible L-L phases makes the experimental separation of carvone more difficult. Simulation results of the batch distillation incorporating the NRTL-RK thermodynamic model indicate that if water, acetone, and t-butanol are previously removed from the reaction mixture, carvone composition can be enriched in the reboiler from 4% up to 50%, or around 86.5% if the removal is in a third distillate cut under vacuum conditions.

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Section: 1catalyst Synthesis and Chemical Reactionsmentioning

confidence: 99%

Section: Experimental Evaluation Of Carvone Separationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Separation of carvone by batch distillation from the mixture obtained from limonene oxidation

Becerra

Villa

2021

Rev.Fac.Ing.Univ.Antioquia

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“…Several citrus oils analyzed in this study, such as orange, tangerine (Ta), lemon (Le), and grapefruits (Gr), from PA (Productos el Arriero Cia. Ltda Colombia) [38], CP (extracted by cold-pressing Brazil) [39], ZUNM (Zhongshan Unicare Natural Medicine Co. China) [40], LAB (Labateca Colombia) [41], SGH (extracted with CH 2 Cl 2 from Sun Groves-Holiday USA) [42], solvent-free microwave extraction (SFMWE) from Citrus paradisi. L Turkey [43], and HD (extracted by hydrodistillation Turkey [44], also have high concentrations of d-limonene ranging from 72.5 to 96 % that depend on the citrus species and the extraction method [11] (see Tab.…”

Section: Research Articlementioning

confidence: 99%

Techno‐Economic Evaluation of d‐Limonene and α‐Pinene Separation from Citrus and Turpentine Oils

Becerra

Villa

2020

Chem Eng & Technol

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The evaluation of the technical and economic separation of the monoterpenes a-pinene and d-limonene from essential oils, carried out by computational simulation of the vacuum fractional distillation in continuous and batch mode from samples of turpentine and citrus oils, was developed using Aspen Plus software combined with estimations of operational expenses (OPEX) and capital expenses (CAPEX) based on the Guthrie method. The production of d-limonene and a-pinene with high purity from the essential oils is a technically feasible process. From the economic point of view and based on the average annual import costs of turpentine and orange oils in Colombia, it was found that the selling prices of a-pinene and d-limonene obtained from the distillation module cost analysis depend on the daily production and can be minimized if essential oils are preliminary extracted from local industrial wastes.

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“…Meanwhile, the production of orange ( Citrus sinensis ) represents more than half of the total citrus fruit production worldwide with an estimate of 73.31 million tons of oranges produced in 2017 [ 52 ]. Though orange peel (OP) contains some important by-products and was traditionally used to obtain essential oils and flavouring compounds [ 39 ], such a level of consumption generates a huge amount of orange peel waste, which eventually ends up in landfills [ 53 ]. More recently, efforts have been made to utilize OP waste either as a carbon activated for catalyst support [ 54 ], as a heterogeneous catalyst for chemical transformations [ 55 , 56 ] and for the production of low-cost biodiesel [ 57 , 58 ].…”

Section: Introductionmentioning

confidence: 99%

Glycolysis of Poly(Ethylene Terephthalate) Using Biomass-Waste Derived Recyclable Heterogeneous Catalyst

et al. 2020

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Plastic production has increased by almost 200-fold annually from 2 million metric tons per year in 1950s to 359 million metric tons in 2018. With this rapidly increasing production, plastic pollution has become one of the most demanding environmental issues and tremendous efforts have been initiated by the research community for its disposal. In this present study, we reported for the first time, a biomass-waste-derived heterogeneous catalyst prepared from waste orange peel for the depolymerisation of poly(ethylene terephthalate) (PET) to its monomer, bis(2-hydroxyethyl terephthalate) (BHET). The prepared orange peel ash (OPA) catalyst was well-characterised using techniques such as IR, inductively coupled plasma (ICP)-OES (Optical Emission Spectrometry), XRD, X-ray fluorescence (XRF), SEM, energy-dispersive X-ray spectroscopy (EDX), TEM, BET (Brunauer-Emmett-Teller) and TGA. The catalyst was found to be composed of basic sites, high surface area, and a notable type-IV N2 adsorption–desorption isotherm indicating the mesoporous nature of the catalyst, which might have eventually enhanced the rate of the reaction as well as the yield of the product. The catalyst completely depolymerises PET within 90 min, producing 79% of recrystallised BHET. The ability of reusing the catalysts for 5 consecutive runs without significant depreciation in the catalytic activity and its eco- and environmental-friendliness endorses this protocol as a greener route for PET recycling.

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A bio-inspired heterogeneous catalyst for the transformation of limonene from orange peel waste biomass into value-added products

Cited by 20 publications

References 48 publications

Separation of carvone by batch distillation from the mixture obtained from limonene oxidation

Separation of carvone by batch distillation from the mixture obtained from limonene oxidation

Techno‐Economic Evaluation of d‐Limonene and α‐Pinene Separation from Citrus and Turpentine Oils

Glycolysis of Poly(Ethylene Terephthalate) Using Biomass-Waste Derived Recyclable Heterogeneous Catalyst

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