Synthesis Of Maleic Anhydride Research Articles

Improving the Barrier and Mechanical Properties of Paper Used for Packing Applications with Renewable Hydrophobic Coatings Derived from Camelina Oil.

This study looked at using modified camelina oil to develop sustainable coatings that could replace those derived from petroleum-based materials for use in packaging and other industrial sectors. Solvent-free synthesis of maleic anhydride grafted camelina oil (MCO) was carried out at two different temperatures (200 and 230 °C) to obtain sustainable hydrophobic coating materials for paper substrates. Maleic anhydride grafting of camelina oil was confirmed with attenuated total reflectance-Fourier transform infrared and NMR spectroscopic techniques, and up to 16% grafting of maleic anhydride was achieved, as determined by the titration method. MCO, obtained at different reaction temperatures, was coated onto cellulosic paper and evaluated for its hydrophobicity, mechanical, oxygen, and water vapor barrier properties. Scanning electron microscopy indicated the homogeneous dispersion of coating material onto the paper substrate. MCO-coated papers (MCO-200C paper and MCO-230C paper) provided a water contact angle of above 90° which indicates that the modified oil was working as a hydrophobic coating. Water vapor permeability (WVP) testing of coated papers revealed a reduction in WVP of up to 94% in comparison to the uncoated paper. Moreover, an improved oxygen barrier property was also observed for paper coated with both types of MCO. Analysis of the mechanical properties showed a greater than 70% retention of tensile strength and up to a five-fold increase in elongation at break of coated versus uncoated papers. Overall, the results show that camelina oil, a renewable resource, can be modified to produce environmentally friendly hydrophobic coating materials with improved mechanical and water vapor barrier properties that can serve as a potential coating material in the packaging industry. The results of this research could find applications in the huge paper packaging industries, specially in food packaging.

A review on the synthesis of maleic anhydride based polyurethanes from renewable feedstock for different industrial applications

A review on the synthesis of maleic anhydride based polyurethanes from renewable feedstock for different industrial applications

Lewis Acids Activated Spontaneous Alternating Copolymerization of Maleic Anhydride and Styrene Derivatives.

Synthesis of maleic anhydride (MA) and styrene (St) copolymers possessing ultra-high molecular weight, strictly alternating regularity and high glass transition temperature simultaneously is still an issure with great challenge. Herein, the spontaneous alternating copolymerization of MA and St derivatives were investigated by using various Lewis acids. In the presence of alkyl aluminum or butyl magnesium, the MA-St alternating copolymers with ultra-high molecular weight (Mn ≤166.5×104 ) and high glass transition temperature (211 °C≤Tg ≤216 °C) were produced and the microstructure of MA-St copolymers were analyzed by 1 H and 13 C NMR spectra. The copolymerizations of MA with St derivatives, including divinylbenzene, p-butenyl styrene, p-methoxystyrene, trans-anethole, p-fluorostyrene and p-chlorostyrene, also were explored by using AlOctyl3 as an activator in toluene at 50 °C.

Novel one-pot microwave synthesis of maleic anhydride based mineral scale inhibitors and their application

This paper presents our research efforts in the discovery of pioneering synthetic routes and designing low molecular-weight maleic-anhydride (MA) homopolymers and MA-n-octyl acrylamide (AAO) copolymers (YMR-series) and their application as scale inhibitors for mineral scales. Hence, the solvent-free, eco-friendly, rapid microwave-assisted method has been developed for the first time to synthesize these antiscalants with higher yield and better efficiency. The inhibition ability on the CaSO4 and CaCO3 scale is 100 % with a 3 ppm dosage level at pH 10.45 and temperature 70 °C.Morphological changes of the CaCO3 and CaSO4 scales due to the strong inhibition action of YMR-series polymers have been studied by scanning electronic microscopy (SEM) and X-ray powder diffraction (XRD) analysis. It is also observed that the anti-scaling effect of the polymers greatly depends on the molecular weight, while MA copolymers show better inhibition efficiency compared to MA homopolymers.

Multicomponent synthesis, DFT calculations and molecular docking studies of novel thiazolyl-pyridazinones as potential antimicrobial agents against antibiotic-resistant bacteria

Novel series of aryl(hetaryl)thiazolylpyridazinedione derivatives were synthesized via one-pot three-component synthesis of maleic anhydride, thiosemicarbazide and the appropriate α-bromoketones using cellulose sulfuric acid (CSA) as an eco-friendly catalyst under microwave irradiation (MWI) in high, efficient yields and short reaction time and the achieved results showed the tremendous synergistic effect between CSA and MWI. All the prepared compounds were fully characterized by spectral methods (IR, Mass, 1H NMR and 13C NMR) and an alternate method. Moreover, in-vitro biological activities of the obtained candidate molecules as antibacterial and/or antifungal agents were investigated against S. aureus, MRSA and C. albicans, and the results were compared with those of standard compounds. The results showed that compound 19 has an excellent antibacterial (S. aureus, MIC: 0.12 μg/mL) and antifungal (C. albicans, MIC: 3.90 μg/mL) activities. In addition, compound 5c demonstrated the highest antibacterial activity against P. aeruginosa (MIC: 0.12 μg/mL). The molecular structures, reactivity and electronic properties of candidate compounds demonstrating the best promising antimicrobial activities were studied at the B3LYP/6–311 G level of theory and their quantum mechanical parameters were computed. The energy gaps of all of the selected compounds were found to range between 3.1 and 3.6 eV. Furthermore, molecular docking with the most common protein receptors of the microorganisms of interest (SAP2 and FabI) was performed.

Oxidative Ring Contraction by a Multifunctional Dioxygenase Generates the Core Cycloocatadiene in the Biosynthesis of Fungal Dimeric Anhydride Zopfiellin.

To elucidate the biosynthesis of a fungicidal dimeric anhydride zopfiellin, the putative biosynthetic gene cluster was identified. We conducted heterologous expression of candidate genes for the synthesis of maleic anhydride and its dimerization and identified the two isomeric dimers with 9-membered rings as products. Notably, α-ketoglutarate-dependent dioxygenase ZopK oxidized one of the dimers, giving the 8-membered ring of zopfiellin. The mechanism of oxidative rearrangement is proposed by analyzing the incorporation of 13C-labeled precursors.

Carbon monoxide oxidation by oxygen in water-acetonitrile solutions of palladium(II) bromide complexes in the presence of Co(II), Fe(II) and Mn(III) phthalocyaninates

Objectives. The objective of this paper was to compare acetylene oxidative dicarbonylation that leads to maleic anhydride with a side reaction of CO oxidation by oxygen in a PdBr 2 -LiBr-H 2 C-CH 3 CN system and in the presence of insoluble (Co) and soluble (Co, Fe, and Mn) phthalocyaninates (PcM). Methods. To study the oxidation of CO to CO 2 , a kinetics method was used; UV and IR spectroscopy was used to determine the concentrations of initial and intermediate compounds. Results . The knetics of CO to CO 2 oxidation were investigated and the reactivity series of PcM in CO oxidation and maleic anhydride synthesis was characterized. A satisfactory correlation was observed between reaction rates and PcM concentration, as well as the nature of metal, in both processes. The IR measurements of concentrations of Pd(II) and Pd(I) intermediate carbonyl complexes, and CO 2 concentrations, have made it possible to hypothesize the mechanism of CO 2 generation. The effect of PcM concentration on the concentrations of Pd(II)(CO) in CO oxidation has been shown. Conclusions. Based on the data regarding CO oxidation and acetylene oxidative dicarbonylation, certain conditions have been proposed to effectively produce double-labeled maleic anhydride with 13 C (from 13 CO).

Millistructured Reactor as Tool for Investigating the Kinetics of Maleic Anhydride Synthesis

AbstractA nearly isothermal millistructured fixed‐bed reactor was used to investigate the kinetics of the selective oxidation of n‐butane to maleic anhydride. In addition to the investigation of a broad range of industrially relevant conditions, the focus was on the influence of the reaction products on the kinetics. For this purpose, a saturator for the accurate dosing of the target product MA was developed. The experimental data were used to derive a reaction network comprising the by‐products acetic and acrylic acid. Additionally, the inhibition of the associated reactions by reactants and products was investigated.

Determination and Application of Improved Kinetic Parameters for Simulation of Maleic Anhydride Synthesis in Industrial Fixed- Bed Reactor

The aims of this study were to determine improved kineticparameters in five kinetic models for oxidation of n-butane intomaleic anhydride in an industrial fixed-bed reactor, and tosimulate the reactor performance. On the basis of the measuredprocess parameters, inlet and outlet concentrations of n-butanewere calculated and then used to fit the kinetic models. Theindustrial fixed-bed reactor was approximated by 10 continuousstirred tank reactors (CSTR) connected in series. Based on thecalculated outlet concentration of n-butane from the industrialreactor, the outlet concentration of n-butane from thepenultimate reactor was calculated. Then the concentrations ofn-butane were calculated until the inlet concentration of nbutanein the first reactor was obtained. Kinetic parameterswere determined by comparing the inlet concentrations of nbutanein the first reactor with the inlet concentration of nbutaneobtained on the basis of the measured processparameters in the industrial fixed-bed reactor. Kinetic modelswith improved kinetic parameters showed better simulationresults compared to kinetic models with the existing kineticparameters. The best agreement of simulation results andmeasured values was achieved with application of the kineticmodel 2 (Equations (2a-c)). The smallest deviations ofnumerical simulation in comparison with measured values of theoutlet pressure of reaction mixture were 0.45, 0.75 and 0.75%for application of the kinetic model 3 (Equations (3a-c)). Thepercentage deviations of numerical simulation with improvedkinetic parameters and the existing kinetic parameters incomparison with measured values of inside reactor temperaturewere in the range 0.90-5.36% and in the range 4.17-9.78%(kinetic model 2, Equations (2a-c)), respectively.

Systematic model‐based design of tolerant chemical reactors

AbstractWith the raw material and energy transition to biomass‐based feedstocks and renewable energy sources, flexible chemical reactor designs which are capable of converting more than one feedstock will become increasingly important in the chemical industry. In the present work, we refer to chemical reactors which can convert multiple different feedstocks to a desired product with a high and consistent quality as tolerant chemical reactors and propose a systematic model‐based design strategy. The proposed design approach is based on the concept of elementary process functions and the so‐called multilevel reactor design (MLRD) methodology. We use a multiscenario formulation to consider different possible feedstock scenarios and formulate a general multi‐objective dynamic optimization problem that is solved using the direct transcription approach in combination with a scalarization method such as, for example, the normal boundary intersection method or the normalized normal constraint method. The proposed approach is illustrated on the synthesis of maleic anhydride from different n‐butenes and n‐butane feedstocks. The resulting segmented fixed‐bed reactor concept is capable of converting the different feedstocks to maleic anhydride while satisfying additional performance and safety constraints. The results highlight the potential of the proposed design approach.

Simulation of commercial fixed-bed reactor for maleic anhydride synthesis: application of different kinetic models and industrial process data

In this study, we have developed a relatively simple mathematical model capable of both simulating the synthesis of maleic anhydride from n-butane in industrial fixed-bed reactor and determining the influences of inlet process parameters on reactor performance. Ten kinetic models were used, and each of them was used in combination with a simplified reactor model. The validation of the developed mathematical model was performed using three process data sets with five process parameters obtained from industrial fixed-bed reactor. The simulation results showed a good agreement with the measured values for three kinetic models. The most influential inlet process parameters are inlet flow rates of n-butane and oxygen. The maleic anhydride yield is more sensitive to the changes of inlet process parameters than n-butane conversion and maleic anhydride selectivity. By increasing the inlet molar flow of n-butane for 20%, n-butane conversion and maleic anhydride yield are decreased for 3.3% and 5.0%, while maleic anhydride selectivity is increased for 6.7%. In order to increase the selectivity of maleic anhydride, it is necessary to decrease the inlet temperature of reaction mixture, the inlet pressure of reaction mixture as well as the inlet molar flow of oxygen, and to increase the inlet molar flow of n-butane.

Tolerant Chemical Reactor Design Exemplified by the Synthesis of Maleic Anhydride

Tolerant Chemical Reactor Design Exemplified by the Synthesis of Maleic Anhydride

Efficient calculation of constraint back-offs for optimization under uncertainty: A case study on maleic anhydride synthesis

In the present work we propose an efficient and general algorithm for optimization under uncertainty based on the work of Srinivasan et al. (2003). We use specialized cubature rules to speed up the uncertainty propagation step which results in a significant reduction of the overall computational effort. The approach is illustrated by studying the optimal design of a fixed bed reactor for the synthesis of maleic anhydride from raffinate II feedstock, where the amount of n-butane and n-butenes in the feed is assumed to be uncertain. Applying the algorithm results in a robustified reactor design which shows significantly less temperature constraint violations and runaway conditions while still satisfying reactor performance criteria such as minimally required conversion and maximum allowable pressure drop.

Highly Efficient Gas-Phase Oxidation of Renewable Furfural to Maleic Anhydride over Plate Vanadium Phosphorus Oxide Catalyst.

Maleic anhydride (MAnh) and its acids are critical intermediates in chemical industry. The synthesis of maleic anhydride from renewable furfural is one of the most sought after processes in the field of sustainable chemistry. In this study, a plate vanadium phosphorus oxide (VPO) catalyst synthesized by a hydrothermal method with glucose as a green reducing agent catalyzes furfural oxidation to MAnh in the gas phase. The plate catalyst-denoted as VPOHT -has a preferentially exposed (200) crystal plane and exhibited dramatically enhanced activity, selectivity and stability as compared to conventional VPO catalysts and other state-of-the-art catalytic systems. At 360 °C reaction temperature with air as an oxidant, about 90 % yield of MAnh was obtained at 10 vol % of furfural in the feed, a furfural concentration value that is much higher than those (<2 vol %) reported for other catalytic systems. The catalyst showed good long-term stability and there was no decrease in activity or selectivity for MAnh during the time-on-stream of 25 h. The high efficiency and catalyst stability indicate the great potential of this system for the synthesis of maleic anhydride from renewable furfural.

A New Process for Maleic Anhydride Synthesis from a Renewable Building Block: The Gas-Phase Oxidehydration of Bio-1-butanol.

We investigated the synthesis of maleic anhydride by oxidehydration of a bio-alcohol, 1-butanol, as a possible alternative to the classical process of n-butane oxidation. A vanadyl pyrophosphate catalyst was used to explore the one-pot reaction, which involved two sequential steps: 1) 1-butanol dehydration to 1-butene, catalysed by acid sites, and 2) the oxidation of butenes to maleic anhydride, catalysed by redox sites. A non-negligible amount of phthalic anhydride was also formed. The effect of different experimental parameters was investigated with chemically sourced 1-butanol, and the results were then confirmed by using genuinely bio-sourced 1-butanol. In the case of bio-1-butanol, however, the purity of the product remarkably affected the yield of maleic anhydride. It was found that the reaction mechanism includes the oxidation of butenes to crotonaldehyde and the oxidation of the latter to either furan or maleic acid, both of which are transformed to produce maleic anhydride.

Nanocarbon structures formation on the electrodes of arc plasmatron

The article presents results of physico-chemical study of the deposit formed on the electrodes of an arc plasmatron when applying propane-butane mixture in the electrode gap. The studies were performed by means of optical, electronic, and Raman microscopy. According to Raman spectra various forms of nanocarbon were identified in the cathode deposit. Fact of synthesis of maleic anhydride and its covalent grafting to nanographite during operation plasmatron was found. It is shown that this construction arc plasmatron with supply of hydrocarbon gas can be considered as a mini-reactor for the synthesis of different forms of nanocarbon, the surface and physical-chemical properties modification.

Proximity risk assessment for two sensitive chemical plants based on the accident scenario consequence analysis

ABSTRACTPetrochemical complexes include high risk interconnected plants processing large quantities of dangerous/flammable substances, complex reactors of high thermal sensitivity operated under severe conditions of high productivity and associated equipment, vessels or separation units operating at intense temperature and pressures. Such plant design/operation problems contribute quite frequently to the occurrence of small incidents or rare major accidents including domino effects. The study applies classical boiling liquid expanding vapour explosion fire and toxic puff release models to evaluate the effects and consequences of different accident scenarios involving two neighbouring risk plants, with exemplifications for the aniline and maleic anhydride synthesis plants. A proposed joint probability index of human casualties, related to thermal radiation doses and toxic material released around plants, points out the influence of production capacity and plant proximity on the severity of accident consequences and domino‐effect occurrence. © 2013 Curtin University of Technology and John Wiley &amp; Sons, Ltd.

Hydrocarbon Selective Oxidation on Vanadium Phosphorus Oxide Catalysts: Insights from Electronic Structure Calculations

The ability of the vanadium phosphorus oxide (VPO) catalyst to selectively activate n-butane and then perform subsequent selective oxidation to maleic anhydride was investigated using electronic structure calculations. Both active site cluster models and periodic surface models, including explicit consideration of surface relaxation and hydration, led to the same qualitative conclusions about the reactivity of the (VO)2P2O7 (1 0 0) surface in substrate adsorption and oxidation. Density functional theory (DFT) reactivity indices and Density of States (DOS) plots show that, whether stoichiometric or phosphorus-enriched, strained or relaxed, bare or hydrated, covalent reactivity at the (1 0 0) surface is controlled by vanadium species, their dual acid–base attack giving selective activation of n-butane via methylene C–H bond cleavage. 1-butene is predicted to chemisorb at the surface using a π-cation complex, the strength of which makes 1-butene an unlikely intermediate in the production of maleic anhydride from n-butane. Coordinatively-unsaturated surface P–O and in-plane P–O–V oxygen species are the most nucleophilic surface oxygens, which may explain the surface-enrichment in phosphorus always seen in industrial catalysts for maleic anhydride synthesis and also recent in situ microscopy images of surface oxygen transfer to n-butane. The resistance of the maleic anhydride selective oxidation product to further transformation was shown to be dependent on its orientation in the active site, and simulation of surface hydration indicated that dissociative adsorption of water may serve to regenerate the catalyst, replenishing its supply of selective nucleophilic oxygen species for mild oxidation.

A concise synthesis of maleic anhydride and maleimide natural products found in Antrodia camphorata

Recently, the natural products maleic anhydride 1 and maleimides 2 and 3 have been isolated from the mycelium of Antrodia Camphorata, each displaying activity in LLC cell lines. We describe a concise synthesis of each of these natural compounds utilizing C–C cross-coupling methodology, namely, the Negishi and Suzuki reactions. This efficient and high yielding synthesis is convergent lending itself to production of medicinal analogues.

Synthesis of Maleic Anhydride Grafted Polypropylene with High Molecular Weight Using Borane/O2 Radical Initiator and Commercial PP Polymers

Synthesis of Maleic Anhydride Grafted Polypropylene with High Molecular Weight Using Borane/O₂ Radical Initiator and Commercial PP Polymers