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Cas Database

108-31-6

108-31-6

Identification

  • Product Name:Maleic anhydride

  • CAS Number: 108-31-6

  • EINECS:203-571-6

  • Molecular Weight:98.0581

  • Molecular Formula: C2H2(CO)2O

  • HS Code:2917 14 00

  • Mol File:108-31-6.mol

Synonyms:2,5-Furandione;Nourymix MA 901;furan-2,5-dione;Dihydro-2,5-dioxofuran;BM 10;Maleic acid anhydride;Maleic Anhydride in Briquettes;cis-Butenedioic anhydride;Toxilic anhydride;

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Safety information and MSDS view more

  • Pictogram(s):CorrosiveC

  • Hazard Codes:C

  • Signal Word:Danger

  • Hazard Statement:H302 Harmful if swallowedH314 Causes severe skin burns and eye damage H317 May cause an allergic skin reaction H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Half-upright position. Refer for medical attention. In case of skin contact First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Give one or two glasses of water to drink. Do NOT induce vomiting. Refer for medical attention . Inhalation causes coughing, sneezing, throat irritation. Skin contact causes irritation and redness. Vapors cause severe eye irritation; photophobia and double vision may occur. (USCG, 1999) Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic acids and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Wear self-contained breathing apparatus for firefighting if necessary. Behavior in Fire: When heated above 148.89°C in the presence of various materials may generate heat and carbon dioxide. Will explode if confined. (USCG, 1999) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: face shield, thermal gloves, chemical protection suit and particulate filter respirator adapted to the airborne concentration of the substance. See Notes. Sweep spilled substance into covered containers. Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Dry. Separated from strong oxidants, strong bases and food and feedstuffs.Keep container tightly closed in a dry and well-ventilated place. Moisture sensitive. Storage class (TRGS 510): Non-combustible, corrosive hazardous materials

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 10 Hr Time-Weighted Avg: 1 mg/cu m (0.25 ppm).Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Usbiological
  • Product Description:Maleic anhydride 99+%
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  • Product Description:Maleic Anhydride >99.0%(GC)(T)
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  • Product Description:Maleic anhydride powder, 95%
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  • Product Description:Maleic anhydride for synthesis. CAS 108-31-6, pH 0.8 (550 g/l, H O, 20 °C) Hydrolysis., for synthesis
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  • Product Description:Maleic anhydride Msynth plus. CAS 108-31-6, pH 0.8 (550 g/l, H O, 20 °C) Hydrolysis., Msynth plus
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  • Product Description:Maleic anhydride Msynth plus. CAS 108-31-6, pH 0.8 (550 g/l, H O, 20 °C) Hydrolysis., Msynth plus
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Relevant articles and documentsAll total 227 Articles be found

Surface dynamics of a vanadyl pyrophosphate catalyst for n-butane oxidation to maleic anhydride: An in situ Raman and reactivity study of the effect of the P/V atomic ratio

Cavani, Fabrizio,Luciani, Silvia,Esposti, Elisa Degli,Cortelli, Carlotta,Leanza, Roberto

, p. 1646 - 1655 (2010)

This work focused on investigating the effect of the P/V atomic ratio in vanadyl pyrophosphate, catalyst for n-butane oxidation to maleic anhydride, on the nature of the catalytically active phase. Structural transformations occurring on the catalyst surface were investigated by means of in situ Raman spectroscopy in a non-reactive atmosphere, as well as by means of steady-state and non-steady-state reactivity tests, in response to changes in the reaction temperature. It was found that the nature of the catalyst surface is affected by the P/V atomic ratio even in the case of small changes in this parameter. With the catalyst having P/V equal to the stoichiometric value, a surface layer made of α-VOPO4 developed in the temperature interval 340400°C in the presence of air; this catalyst gave a very low selectivity to maleic anhydride in the intermediate T range (340-400°C). However, at 400440°C δ-VOPO4 overlayers formed; at these conditions, the catalyst was moderately active but selective to maleic anhydride. With the catalyst containing a slight excess of P, the ratio offering the optimal catalytic performance, δVOPO4 was the prevailing species over the entire temperature range investigated (340-440°C). Analogies and differences between the two samples were also confirmed by reactivity tests carried out after in situ removal and reintegration of P. These facts explain why the industrial catalyst for n-butane oxidation holds a slight excess of P; they also explain discrepancies registered in the literature about the nature of the active layer in vanadyl pyrophosphate.

Structure Sensitivity of the Catalytic Oxidation of n-Butane to Maleic Anhydride

Cavani, Fabrizio,Centi, Gabriele,Trifiro, Ferruccio

, p. 492 - 494 (1985)

Disorder along the (020) cleavage plane of the (VO)2P2O7 catalyst considerably enhances the activity of the selective oxidation of n-butane to maleic anhydride.

ΑII-(V1-xWx)OPO4 catalysts for the selective oxidation of n-butane to maleic anhydride

Schulz,Roy,Wittich,d'Alnoncourt, R. Naumann,Linke,Strempel,Frank,Glaum,Rosowski

, p. 113 - 119 (2019)

The vanadyl pyrophosphate (VPP) based catalyst is unique in converting n-butane selectively (60–70%) into maleic anhydride (MAN), whereas a MAN selectivity of 20% may be regarded as high for structurally different catalyst systems. We present novel vanadium phosphorus oxides and mixed metal phosphate solid solutions tested for n-butane oxidation to MAN with a selectivity of >30%. The majority of the catalysts were prepared by solution combustion synthesis. (V1-xWx)OPO4 with αII structure was found to be more active and selective in the oxidation of n-butane compared to β-VOPO4. By adjusting the tungsten content the oxidation state of vanadium in (V1-xWx)OPO4 can be tuned between 4.74 and 4.99, which is regarded as a key factor for MAN production. All catalysts were structurally stable, but the specific surface area increased during the reaction, as detected by X-ray diffraction and N2 physisorption, respectively. (V1-xMox)OPO4 was also stable, but the MAN selectivity was lower compared to β-VOPO4. Low conversions result from the low surface area of the screening samples, however, could be overcome by advanced synthesis protocols.

In Situ FTIR Spectroscopy of 1-Butene and 1,3-Butadiene Selective Oxidation to Maleic Anhydride on V-P-O Catalysts

Wenig, Robert W.,Schrader, Glenn L.

, p. 1911 - 1918 (1987)

The selective oxidation of 1-butene and 1,3-butadiene was studied by transmission infrared spectroscopy.Vanadium-phosphorous-oxygen catalysts prepared by the reaction of V2O5 with H3PO4 in alcohol solution were used.Infrared spectra were collected in situ during the flow of 75 cm3 of 1.5percent hydrocarbon-in-air mixtures over catalysts having P-to-V ratios of 0.9, 1.0, and 1.1.Reaction temperatures from 300 to 400 deg C were investigated with 1-butene feeds, whereas the highly reactive 1,3-butadiene was studied only at 300 deg C.An adsorbed butadiene species, maleic acid, maleic anhydride were observed during both olefin partial oxidation studies.Evidence was obtained for a second olefin species which had been previously observed for in situ n-butane selective oxidation studies.Concentrations of adsorbed species were found to vary with catalyst phosphorous loading, reaction temperature, and time of exposure to reaction conditions.

In situ Raman spectroscopic investigation of surface redox mechanism of vanadyl pyrophosphate

Koyano, Gaku,Saito, Takaya,Misono, Makoto

, p. 415 - 416 (1997)

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Activity and Selectivity in Catalytic Reactions of Buta-1,3-diene and But-1-ene on Supported Vanadium Oxides

Mori, Kenji,Miyamoto, Akira,Murakami, Yuichi

, p. 13 - 34 (1986)

The activity and selectivity in the oxidation of buta-1,3-diene, and oxidation and isomerization of but-1-ene on unsupported and supported V2O5 catalysts have been investigated in terms of the catalyst structure.The rate of oxidation is mainly determined by the number of surface V=O species on the catalyst for both buta-1,3-diene and but-1-ene.The roughness of the V2O5 surface affected the activity for buta-1,3-diene, but not for but-1-ene oxidation.It was also found that TiO2 support increases the activity of the surface V=O for but-1-ene oxidation.The selectivity to maleic anhydride was determined by the number of V2O5 layers on the support for both reactions.When the number of V2O5 layers was 1 or 2, the selectivity was low, while it increased markedly with an increase in the number of V2O5 layers to 5, and attained a constant value above 5 layers.Both V2O5 and support were active for the isomerization of but-1-ene to cis- and trans-but-2-ene.On V2O5, the cis/trans ratio was low, while it was as high as 3 for the Al2O3 support.The rate and selectivity of the isomerization on supported catalysts were explained in terms of the structure of V2O5 on the support.Difference in the structure-activity/selectivity correlation between oxidation and isomerization and that between but-1-ene oxidation and buta-1,3-diene oxidation were also discussed.

Effects of cobalt additive on amorphous vanadium phosphate catalysts prepared using precipitation with supercritical co2 as an antisolvent

Lopez-Sanchez, J. Antonio,Bartley, Jonathan K.,Burrows, Andrew,Kiely, Christopher J.,Haevecker, Michael,Schloegl, Robert,Volta, Jean Claude,Poliakoff, Martin,Hutchings, Graham J.

, p. 1811 - 1816 (2002)

The effect of addition of cobalt to an amorphous vanadium phosphate for the selective oxidation of n-butane to maleic anhydride is described and discussed. Cobalt is a well known promoter for crystalline vanadium phosphate catalysts and is most effective at a concentration of 1 atom % relative to vanadium. In contrast, for amorphous vanadium phosphate materials, prepared by precipitation using supercritical CO2 as an antisolvent, cobalt appears to act as a catalyst poison, decreasing both the catalyst activity and selectivity for maleic anhydride. Detailed analysis by transmission electron microscopy, 31P spin echo mapping NMR spectroscopy and X-ray absorption spectroscopy is described, which highlight differences with the unmodified catalyst. It is concluded that the addition of cobalt affects the morphology of the material and the oxidation state of vanadium, and that these changes deleteriously affect the catalytic performance.

-

Cherbuliez,E. et al.

, p. 458 - 464 (1960)

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Surface Acidity of Vanadyl Pyrophosphate, Active Phase in n-Butane Selective Oxidation

Busca, Guido,Centi, Gabriele,Trifiro, Ferruccio,Lorenzelli, Vincenzo

, p. 1337 - 1344 (1986)

The surface acidity of two (VO)2P2O7catalysts with similar specific activities per square meter of surface area in 1-butene selective oxidation, but different specific activities in n-butane selective oxidation, was studied by ammonia, pyridine, acetonitrile, CO, and CO2 adsorption, by ammonia temperature-programmed desorption, and by 2-propanol oxidation.The results for both catalysts indicate the presence of strong Broensted sites attributed to surface P-OH groups and of medium strong Lewis sites attributed to V(IV) coordinatively unsaturated ions exposed on the surface.The presence of these centers was related to the (VO)2P2O7 structure itself and is fairly independent of the (VO)2P2O7 preparation method.However, in the (VO)2P2O7 prepared in an organic medium and to a lesser extent in the (VO)2P2O7 prepared in an aqueous medium, the presence of very strong Lewis sites also was observed.The enhancement of the rate of n-butane activation in the (VO)2P2O7 prepared in an organic medium was attributed to the presence of these sites.The role of the preparation method in the formation of such very strong Lewis sites also is discussed.

-

Ai

, p. 761,762-765 (1971)

-

-

Ai

, p. 2766,2767 (1979)

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Preparation and characterization of vanadyl hydrogen phosphate hydrates; VO(HPO4)*1.5 H2O and VO(HPO4)*0.5 H2O

Matsuura, Ikuya,Ishimura, Tomohiro,Kimura, Naomasa

, p. 769 - 770 (1995)

A new phase of vanadyl(IV) hydrogen phosphate sesquihydrate, VO(HPO4)*1.5 H2O, has been obtained by the reduction of VOPO4*2H2O with 1-butanol.The unit cell is the orthorhombic system with lattice constants a=7.43 Angstroem, b=9.62 Angstroem, and c=7.97 Angstroem in space group Pmmn.

-

Varma,Saraf

, p. 361,365,366,371 (1978)

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X-Ray Study of a Vanadium-Phosphorus Mixed Oxide Catalyst for Selective Butane Oxidation to Maleic Anhydride

Bergeret, G.,Broyer, J. P.,David, M.,Gallezot, P.,Volta, J. C.,Hecquet, G.

, p. 825 - 826 (1986)

The radical electron distribution obtained from X-ray patterns has been used to study the structure of a poorly-crystalline vanadium-phosphorus mixed oxide (VPO) catalyst after selective oxidation of n-butane; the effective catalyst consists of a mixture of a crystallized (VO)2P2O7 phase (V(4+)) and an amorphorus VPO phase (V(5+)) showing many corner-sharing VO6 octahedra.

NATURE OF THE DONOR-ACCEPTOR REACTION OF MALEIC ANHYDRIDE WITH THE VINYL ETHER OF BENZYL ALCOHOL

Petrova, T. L.,Smirnov, A. I.,Ratovskii, G. V.,Chuvashev, D. D.,Modonov, V. B.,et al.

, p. 1371 - 1376 (1985)

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Effects of Consecutive Oxidation on the Production of Maleic Anhydride in Butane Oxidation over Four Kinds of Well-Characterized Vanadyl Pyrophosphates

Igarashi, Hiroshi,Tsuji, Katsuyuki,Okuhara, Toshio,Misono, Makoto

, p. 7065 - 7071 (1993)

Factors determining the selectivity of butane oxidation at high conversion levels have been examined by using four kinds of well-characterized vanadyl pyrophosphate catalysts (C-1 - C-4) in kinetic experiments.The catalysts were carefully characterized by scanning electron microscopy, X-ray powder diffraction, X-ray photoelectron spectroscopy, and infrared spectroscopy and were made of a single crystalline phase of vanadyl pyrophosphate, (VO)2P2O7.C-1 was prepared by reduction with NH2OH*HCl and consisted of large particles (5 μm) and small particles (0.2 μm).The particles of C-2 obtained from V2O4 had a size of 2 μm.C-3, which was obtained by an organic solvent method, showed a rose-like structure.C-4 from VOPO4*2H2O had a large plate-like structure (5 μm).While all of the catalysts exhibited similar selectivities for the formation of maleic anhydride (63-72 percent) at low conversion levels, the extend of selecticity decreases with an increase in the conversion and strongly depends on the catalysts.It also correlates oppositely with the catalytic activity for the oxidation of maleic anhydride, measured separately.This indicates that the consecutive oxidation of product maleic anhydride is a crucial factor for the selectivity at high conversions.A simulation using a model that includes the consecutive oxidation of maleic anhydride, in which the experimental rate constants for the oxidation of butane and maleic anhydride have been used, reproduced the selectivity-conversion curves experimentally observed.

Diels-Alder reaction of vinylene carbonate and 2,5-dimethylfuran: Kinetic vs. thermodynamic control

Taffn, Celine,Kreutler, Glenda,Bourgeois, Damien,Clot, Eric,Perigaud, Christian

, p. 517 - 525 (2010)

The Diels - Alder reaction between 2,5-dimethylfuran and vinylene carbonate was studied, both from an experimental and a theoretical point of view. The system was shown to slowly reach a thermodynamic equilibrium, characterized by the almost exclusive formation of the exo isomer. We rationalized these results by a comparison with classical systems involving maleic anhydride, and highlighted the different reactivity of vinylene carbonate as a dienophile. Finally, a preparative scale synthesis of pure exo isomer 4, a potentially useful synthon, ensued from this work. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2010.

Fundamental studies of butane oxidation over model-supported vanadium oxide catalysts: Molecular structure-reactivity relationships

Wachs, Israel E.,Jehng, Jih-Mirn,Deo, Goutam,Weckhuysen, Bert M.,Guliants,Benziger,Sundaresan

, p. 75 - 88 (1997)

The oxidation of n-butane to maleic anhydride was investigated over a series of model-supported vanadia catalysts where the vanadia phase was present as a two-dimensional metal oxide overlayer on the different oxide supports (TiO2, ZrO2, CeO2, Nb2O5, Al2O3, and SiO2). No correlation was found between the properties of the terminal V=O bond and the butane oxidation turnover frequency (TOF) during in situ Raman spectroscopy study. Furthermore, neither the n-butane oxidation TOF nor maleic anhydride selectivity was related to the extent of reduction of the surface vanadia species. The n-butane oxidation TOF was essentially independent of the surface vanadia coverage, suggesting that the n-butane activation requires only one surface vanadia site. The maleic anhydride TOF, however, increased by a factor of 2-3 as the surface vanadia coverage was increased to monolayer coverage. The higher maleic anhydride TOF at near monolayer coverages suggests that a pair of adjacent vanadia sites may efficiently oxidize n-butane to maleic anhydride, but other factors may also play a contributing role (increase in surface Bronsted acidity and decrease in the number of exposed support cation sites). Varying the specific oxide support changed the n-butane oxidation TOF by ca. 50 (Ti > Ce > Zr ~ Nb > Al > Si) as well as the maleic anhydride selectivity. The maleic anhydride selectivity closely followed the Lewis acid strength of the oxide support cations, Al > Nb > Ti > Si > Zr > Ce. The addition of acidic surface metal oxides (W, Nb, and P) to the surface vanadia layer was found to have a beneficial effect on the n-butane oxidation TOF and the maleic anhydride selectivity. The creation of bridging V-O-P bonds had an especially positive effect on the maleic anhydride selectivity.

Ionization and Intramolecular Reactions of N,N-Bis- and N,N-Bismaleamic Acids. An Enzyme Model

Suh, Junghun,Kim, Mahn Joo,Seong, Nak Jin

, p. 4354 - 4358 (1981)

N,N-Bismaleamic acid (1) and N,N-bismaleamic acid (2) underwent exclusive amide hydrolysis and intramolecular Michael-type addition, respectively.The pH profile of the pseudo-first-order rate constant for the reaction of 1 was a simple descending sigmoid inflecting at the pKa of the carboxyl group.The pH profile of 2 was a composite of two bell-shaped curves which disclosed the abnormally low pKa's of the carboxyl group and one of the two pyridinium groups.The change in the reaction path and the abnormal pKa's observed withthe structural variation in maleamic acid derivatives suggest that the change in enzyme specificity and the perturbed pKa's of the active site functional groups can be achieved with a relatively loose geometry of the enzyme-substrate complex.The failure to observe the metal ion catalysis of the amide hydrolysis of 1 and 2 indicates that the metal complexation of the compounds is inefficient.

Selective aerobic oxidation of furfural to maleic anhydride with heterogeneous Mo-V-O catalysts

Li, Xiukai,Ho, Ben,Zhang, Yugen

, p. 2976 - 2980 (2016)

A heterogeneous catalytic system using binary Mo-V metal oxides as catalysts was demonstrated for the selective aerobic oxidation of furfural to maleic anhydride (MA). Aspects such as the solvent for the reaction, the phase composition and the Mo/V ratio for the catalyst, and other reaction conditions were investigated in detail. Up to 65% yield of MA was achieved over the Mo4VO14 catalyst in an acetic acid solvent under optimal conditions. The catalyst could be recycled. The reaction mechanism and the role of the acetic acid solvent were also discussed.

Significant catalytic recovery of spent industrial DuPont catalysts by surface deposition of an amorphous vanadium-phosphorus oxide phase

Blanco, Raquel Mateos,Shekari, Ali,Carrazán, Silvia González,Bordes-Richard, Elisabeth,Patience, Gregory S.,Ruiz, Patricio

, p. 48 - 52 (2013)

DuPont's vanadium phosphorous oxide catalyst (VPO) deactivated with time-on-stream in a commercial butane to maleic anhydride reactor. Coincidentally, V5+ phases formed on the surface (based on XPS)-principally β-VOPO4 but also V2O5. This catalyst was reactivated by introducing a small amount of a VPO (theoretical P/V atomic ratio = 0.86) phase. The maleic anhydride production rate of the reactivated catalyst was higher by about 60% compared to the used catalyst. n-Butane conversion increased by about 50% and the selectivity to maleic anhydride improved by 15%. The analyses of the modified catalyst by X-ray diffraction, Raman spectroscopy and X-ray photoelectron spectroscopy showed that the V2O5 and β-VOPO4 phases disappeared and suggested that an amorphous phase formed on the surface. The treatment resulted in a lower V5+/V4+ and P/V ratios on the used catalyst surface.

Selectivity and Activity in the Oxidation of Benzene, 1-Butene, and 1,3-Butadiene on Supported Vanadium Oxide Catalysts

Mori, Kenji,Inomata, Makoto,Miyamoto, Akira,Murakami, Yuichi

, p. 4560 - 4561 (1983)

Selectivity with respect to partial oxidation products in the oxidation of benzene, 1-butene, and 1,3-butadiene on V2O5/TiO2 and V2O5/Al2O3 catalysts is determined by the number of V2O5 layers on the support, while the activity is controlled by the number of surface V=O species on the catalyst.

Synthesis of vanadium phosphorus oxide catalysts promoted by iron-based ionic liquids and their catalytic performance in selective oxidation of: n -butane

Dai, Fei,Li, Zihang,Chen, Xuejing,He, Bin,Liu, Ruixia,Zhang, Suojiang

, p. 4515 - 4525 (2018)

A series of vanadium phosphorus oxide (VPO) catalysts have been firstly synthesized using iron-based ionic liquids (ILs) as additives for selective oxidation of n-butane to maleic anhydride (MA) in this work. Meanwhile, VPO catalysts doped with inorganic iron salts were also prepared for comparison. The catalytic evaluation presented that iron-based IL modification remarkably enhanced the n-butane conversion and MA yield. A combination of techniques including XRD, Raman, TG, BET, SEM, TEM, XPS and H2-TPR was employed to investigate the intrinsic distinction among these catalysts. The results demonstrated that iron-based ILs notably change the morphology of the VPO catalyst from a plate-like structure into chrysanthemum-shape clusters, leading to a significant increase in the surface area of the catalyst, and largely promote the formation of (VO)2P2O7. All of these were closely associated with the synergistic effect existing between the structure-oriented cations and metal anions in ILs during the preparation of the VPO catalyst. In addition, the differences in the structure and redox properties of the catalysts studied were also discussed and compared with those doped with conventional inorganic salt additives.

Comparison of pH-sensitive degradability of maleic acid amide derivatives

Kang, Sunyoung,Kim, Youngeun,Song, Youngjun,Choi, Jin Uk,Park, Euddeum,Choi, Wonmin,Park, Jeongseon,Lee, Yan

, p. 2364 - 2367 (2014)

We synthesized five maleic acid amide derivatives (maleic, citraconic, cis-aconitic, 2-(2′-carboxyethyl) maleic, 1-methyl-2-(2′- carboxyethyl) maleic acid amide), and compared their degradability for the future development of pH-sensitive biomaterials with tailored kinetics of the release of drugs, the change of charge density, and the degradation of scaffolds. The degradation kinetics was highly dependent upon the substituents on the cis-double bond. Among the maleic acid amide derivatives, 2-(2′-carboxyethyl) maleic acid amide with one carboxyethyl and one hydrogen substituent showed appropriate degradability at weakly acidic pH, and the additional carboxyl group can be used as a pH-sensitive linker.

The conversion of 5-hydroxymethyl furfural (HMF) to maleic anhydride with vanadium-based heterogeneous catalysts

Li, Xiukai,Zhang, Yugen

, p. 643 - 647 (2016)

Heterogeneous catalytic systems using vanadium-based solid catalysts with or without silica support were developed for the oxidation of 5-hydroxymethyl furfural (HMF) to maleic anhydride (MA) and up to 79% yield of MA was achieved. Both unsupported and silica supported vanadium oxide catalysts showed high activity, selectivity, and recyclability. The direct conversion of fructose to MA via the HMF intermediate was further demonstrated and over 50% overall yield of MA was achieved.

Effect of direct ultrasound synthesis via a sesquihydrate route on bismuth-promoted vanadyl pyrophosphate catalysts

Goo, Kang-Zhi,Yap, Yeow-Hong,Lin, Kuen-Song,Leong, Loong-Kong

, p. 94 - 102 (2020)

A series of 1, 3, and 5% Bi-doped vanadium phosphate catalyst catalysts were prepared via sesquihydrate route using direct ultrasound method and were denoted as VPSB1, VPSB3, and VPSB5, respectively. These catalysts were synthesized solely using a direct ultrasound technique and calcined in a n-butane/air mixture. This study showed that catalyst synthesis time can be drastically reduced to only 2 hr compared to conventional 32–48 hr. All Bi-doped catalysts exhibited a well-crystallized (VO)2P2O7 phase. In addition, two V5+ phases, that is, β-VOPO4 and αII-VOPO4, were observed leading to an increase in the average oxidation state of vanadium. All catalysts showed V2p3/2 at approx. 517 eV, giving the vanadium oxidation state at approx. 4.3–4.6. Field-emission scanning electron microscopy micrographs showed the secondary structure consisting of thin and small plate-like crystal clusters due to the cavitation effect of ultrasound waves. VPSB5 showed the highest amount of oxygen species removed associated with the V5+ and V4+ species in temperature-programmed reduction in H2 analyses. TheX-ray absorption near edge structure (XANES) measurement showed the occurrence of vanadium oxide reductions in hydrogen gas flow, indicating the presence of V4+ and V5+ species. Higher average valence states of V5+, indicating more V5+ phases, were present. The addition of bismuth has increased the activity and selectivity to maleic anhydride.

Spectroscopic Investigation of Vanadium-Phosphorus Catalysts

Martini, Giacomo,Trifiro, Ferruccio,Vaccari, Angelo

, p. 1573 - 1576 (1982)

The structural and surface changes occurring in vanadium-phosphorus mixed oxides with P/V atomic ratios in the 1.0 - 1.8 range prepared by reducing the V(V) with oxalic acid were investigated by ESR, diffuse reflectance spectroscopy, X-ray diffraction, and redox titrimetry.Poorly crystallized α-VOPO4 was formed for a P/V ratio of 1.0, and new phases containing V(IV) were found as the P/V ratio increased.The V(IV) centers changed progressively from isolated, dispersed ions in a α-VOPO4 matrix into a V(IV) phosphate phase, as revealed by ESR and diffuse reflectance spectra.These results are compared with catalytic activity data for the 1-butene oxidation in a pulse reactor.The highest yield of maleic anhydride was given by the samples with a 1.0 - 1.2 P/V ratio, indicating that VOPO4 with dispersed V(IV) ions is the active phase.

Towards physical descriptors of active and selective catalysts for the oxidation of n-butane to maleic anhydride

Eichelbaum, Maik,Glaum, Robert,Haevecker, Michael,Wittich, Knut,Heine, Christian,Schwarz, Heiner,Dobner, Cornelia-Katharina,Welker-Nieuwoudt, Cathrin,Trunschke, Annette,Schloegl, Robert

, p. 2318 - 2329 (2013)

Based on our newly developed microwave cavity perturbation technique, the microwave conductivity of diverse vanadium(III), (IV), and (V) phosphate catalysts was measured under reaction conditions for the selective oxidation of n-butane. The conductivity response on the gas phase was identified as a very sensitive measure for the redox kinetics, reversibility, and stability of the samples, which are important prerequisites for highly selective and active catalysts. The sensitivity achieved by our method was comparable to surface-sensitive methods such as X-ray photoelectron spectroscopy, whereas more conventional analytic techniques such as X-ray diffractometry or Raman spectroscopy only indicated the stability of the bulk crystal phase under the same reaction conditions.

Influence of starting solution in preparation of V2O5/TiO2 catalysts for selective oxidation of benzene

Satsuma, Atsushi,Takenaka, Sakae,Tanaka, Tsunehiro,Nojima, Shigeru,Kera, Yoshiya,Miyata, Hisashi

, p. 1115 - 1116 (1996)

The selectivity in benzene oxidation over V2O5/TiO2(rutile) was drastically changed with starting solutions in the preparation of catalysts, although V2O5/TiO2(rutile) prepared from oxalic acid solution of NH4VO3 selectively oxidized benzene to maleic anhydride, only a total oxidation proceeded over those prepared without oxalic acid.

Surface Dynamics of Adsorbed Species on Heterogeneous Oxidation Catalysts: Evidence from the Oxidation of C4 and C5 Alkanes on Vanadyl Pyrophosphate

Busca, Guido,Centi, Gabriele

, p. 46 - 54 (1989)

Steady-state and transient reactivity measurements, Fourier-transform infrared studies, and stopped-flow desorption analyses of the selective oxidation of C4 and C5 alkanes at the vanadyl pyrophosphate surface suggest that the surface dynamics of adsorbed species plays an important role in determining the selective oxidation pathways and the nature of the products of selective oxidation.The results indicate the possibility of two different oxidation pathways in maleic anhydride synthesis from n-butane which involve the intermediate formation of either a lactone or furan and which are characterized by different rates and selectivities.The presence of side methyl groups in the formation of similar intermediates from n-pentane decreases their reactivity and favors a parallel surface reaction between intermediates with the final formation of phthalic anhydride from the C5 hydrocarbon.However, when the rate of conversion of the intermediates is increased, thus modifying the surface availability of oxygen, maleic anhydride also becomes the principal product from the C5 alkane.

A good performance VPO catalyst for partial oxidation of n-Butane to maleic anhydride

Wang, Xiaoshu,Nie, Weiyan,Ji, Weijie,Guo, Xuefeng,Yan, Qijie,Chen, Yi

, p. 696 - 697 (2001)

A VPO catalyst prepared by the reaction of vanadium pentoxide and isobutyl alcohol/benzyl alcohol in the presence of polyethylene glycol with the molecular weight of 2000 (PEG2000) was found to be highly selective and active for the conversion of n-butane to maleic anhydride.

Catalytic Synthesis of 2,5-Furandicarboxylic Acid from Concentrated 2,5-Diformylfuran Mediated by N-hydroxyimides under Mild Conditions

Xia, Fei,Ma, Jiping,Jia, Xiuquan,Guo, Meiling,Liu, Xuebin,Ma, Hong,Gao, Jin,Xu, Jie

, p. 3329 - 3334 (2019)

Producing polyester monomer 2,5-furandicarboxylic acid (FDCA) from biomass as an alternative to fossil-derived terephthalic acid has drawn much attention from both academy and industry. In this work, an efficient FDCA synthesis was proposed from 10.6 wt % 2,5-diformylfuran (DFF) in acetic acid using a combined catalytic system of Co/Mn acetate and N-hydroxyimides. The intermediate product of 5-formyl-2-furandicarboxylic acid (FFCA) possesses the least reactive formyl group. N-hydroxysuccinimide was found to be superior to N-hydroxyphthalimide in catalyzing the oxidation of the formyl group in FFCA intermediate, affording a near 95 % yield of FDCA under mild conditions of 100 °C. Trace maleic anhydride was detected as by-product, which mainly came from the oxidative cleavage of DFF via furfural, furoic acid and 5-acetoxyl-2(5H)-furanone as intermediates.

On the Role of the VO(H2PO4)2 Precursor for n-Butane Oxidation into Maleic Anhydride

Sananes, M. T.,Hutchings, G. J.,Volta, J. C.

, p. 253 - 260 (1995)

The catalytic role of VO(H2PO4)2, the precursor of the V O(PO3)2 phase, has been studied for n-butane oxidation to maleic anhydride.By comparison with the activated VPO catalyst, derived from the VOHPO4*0.5H2O precursor phase, VO(H2PO4)2 gives a highly selective final catalyst.The total oxidation products CO and CO2 are not observed under any of the conditions examined, a result confirmed by extensive catalyst testing and carbon mass balances.The final catalyst derived from VO(H2PO4)2 has a low surface area, ca. 1 m2/g, and consequently demonstrates low specific activity on the basis of n-butane conversion per unit mass.However, the interinsic activity (activity per unit surface area) is found to be higher than that for catalysts derived from VOHPO4 * 0.5H2O.Since some VO(H2PO4)2 is present in VOHPO4 * 0.5H2O, which is the precursor of the industrial catalyst, the results of this study complicate the simple model in which the (VO)2P2O7 phase derived from VOHPO4 * 0.5H2O is responsible for the selective oxidation of n-butane.The observation that the precursor VO(H2PO4)2 can generate catalysts of high specific activity and of total selectivity to partial oxidation products might provide a useful insight into the design of a new series of high activity and high selectivity partial oxidation catalysts.

The consequences of support identity on the oxidative conversion of furfural to maleic anhydride on vanadia catalysts

Santander, Paola,Bravo, Luis,Pecchi, Gina,Karelovic, Alejandro

, (2020)

Maleic anhydride (MA) is a high value building block molecule whose synthesis from furfural (FUR) is proposed as a green and sustainable alternative. In this work, vanadia supported on SiO2, γ-Al2O3, ZrO2 and TiO2 catalysts were synthetized, characterized and investigated for the selective gas phase oxidation of FUR to MA. The catalytic properties depend on both, the nature of the support and the vanadia surface dispersion. V2O5/SiO2 and V2O5/γ-Al2O3 display ca. 50 % MA yield. Conversely, for the V2O5/ZrO2 and V2O5/TiO2 catalysts, complete FUR oxidation to CO2 and negligible MA production was obtained. By decreasing the oxidation potential of the reaction feed, V2O5/ZrO2 and V2O5/TiO2 catalysts achieve MA yields comparable to V2O5/SiO2 and V2O5/γ-Al2O3 catalysts. This behavior is attributed to the higher vanadia dispersion on ZrO2 and TiO2 and the reducible nature of these supports. The results obtained in this work offer new catalytic alternatives for the sustainable production of MA.

Vanadium-oxo immobilized onto Schiff base modified graphene oxide for efficient catalytic oxidation of 5-hydroxymethylfurfural and furfural into maleic anhydride

Lv, Guangqiang,Chen, Chunyan,Lu, Boqiong,Li, Jinlong,Yang, Yongxing,Chen, Chengmeng,Deng, Tiansheng,Zhu, Yulei,Hou, Xianglin

, p. 101277 - 101282 (2016)

Graphene oxide (GO) sheets are emerging as a new class of carbocatalyst, and also a perfect platform for molecular engineering. The hydroxyl groups on either side of GO sheets can function as anchors by employing them as scaffolds linking organometallic nodes and vanadium-oxo was homogeneously immobilized on a Schiff base modified GO support via covalent bonding. The developed VO-NH2-GO was shown to be an efficient and recyclable heterogeneous catalyst for the aerobic oxidation of 5-hydroxymethylfurfural (HMF) into maleic anhydride. Up to 95.3% yield of maleic anhydride from HMF and 62.4% from furfural were achieved under optimized reaction conditions. The immobilized vanadium oxo was identified as the active sites, while the residual oxygen-containing groups worked synergistically to adsorb HMF to maintain a high reactant concentration around the catalyst. The STY value was enhanced significantly over VO-NH2-GO, compared with homogeneous or heterogeneous traditional supported V based catalyst.

EFFECT OF THE STRUCTURE OF METHYL-SUBSTITUTED CARBOXYLIC ACIDS AND ANHYDRIDES ON THEIR ACTIVITY IN GAS-PHASE OXIDATION

Sharipov, A. Kh.,Masagutov, R. M.,Rafikov, S. R.

, p. 817 - 820 (1982)

-

Kinetic and structural understanding of bulk and supported vanadium-based catalysts for furfural oxidation to maleic anhydride

Bravo, Luis,Gómez-Cápiro, Oscar,Karelovic, Alejandro,Lagos, Patricio,Pecchi, Gina,Santander, Paola

, p. 6477 - 6489 (2021)

The kinetics of gas-phase furfural partial oxidation to maleic anhydride (MA) was studied over bulk vanadium-phosphorus-based catalysts obtained by aqueous (VPAq) and organic (VPOr) methods and compared to a supported V2O5/Al2O3 catalyst. The solids were characterized by N2 adsorption-desorption, XRD and UV-vis DRS. Results showed a higher specific surface area on VPOr compared with VPAq materials, with a well-defined (VO)2P2O7 crystalline structure. UV-vis analysis showed mainly V(v) on VPAq and an intermediate state between V(iv) and V(v) on VPOr. A detailed kinetic study demonstrated that furfural can be oxidized to MA or COx through parallel paths. At high oxygen partial pressures MA oxidation is inhibited on VPO catalysts but favored on V2O5/Al2O3. A Langmuir-Hinshelwood kinetic model with negligible site occupancy fits the experimental data with a 16% mean error. It also shows a higher apparent activation energy for furfural partial oxidation than for complete oxidation, highlighting the favored selectivity to maleic anhydride at higher temperatures on VPO catalysts.

The electronic factor in alkane oxidation catalysis

Eichelbaum, Maik,H?vecker, Michael,Heine, Christian,Wernbacher, Anna Maria,Trunschke, Annette,Schl?gl, Robert,Rosowski, Frank

, p. 2922 - 2926 (2015)

This article addresses the fundamental question of whether concepts from semiconductor physics can be applied to describe the working mode of heterogeneous oxidation catalysts and whether they can be even used to discriminate between selective and unselective reaction pathways. Near-ambient-pressure X-ray photoelectron spectroscopy was applied to the oxidation of n-butane to maleic anhydride on the highly selective catalyst vanadyl pyrophosphate and the moderately selective MoVTeNbOx M1 phase. The catalysts were found to act like semiconducting gas sensors with a dynamic charge transfer between the bulk and the surface, as indicated by the gas-phase-dependent response of the work function, electron affinity, and the surface potential barrier. In contrast, only a minor influence of the gas phase on the semiconducting properties and hence no dynamic surface potential barrier was monitored for the total oxidation catalyst V2O5. The surface potential barrier is hence suggested as descriptor for selective catalysts.

Brown,Frozer

, p. 2917,2918 (1942)

Hydroxyapatite-Supported Polyoxometalates for the Highly Selective Aerobic Oxidation of 5-Hydroxymethylfurfural or Glucose to 2,5-Diformylfuran under Atmospheric Pressure

Guan, Hongyu,Li, Ying,Wang, Qiwen,Wang, Xiaohong,Yu, Hang

, p. 997 - 1005 (2021)

(NH4)5H6PV8Mo4O40 supported on hydroxyapatite (HAP) (PMo4V8/HAP (n)) was prepared through the ion exchange of hydroxy groups. This ion exchange favored the oxidative conversion of 5-hydroxymethylfurfural (5-HMF) to 2,5-diformylfuran (DFF) in a one-pot cascade reaction with 96.0 % conversion and 83.8 % yield under 10 mL/min of O2 flow. PMo4V8/HAP (31) was used to explore the production of DFF directly from glucose with the highest yield of 47.9 % so far under atmospheric oxygen, whereas the yield of DFF increased to 54.7 % in a one-pot and two-step reaction. These results indicated that the active sites in PMo4V8/HAP (31) retained their activities without any interference toward one another, which enabled the production of DFF in a more cost-saving way by only using oxygen and one catalyst in a one-step reaction. Meanwhile, the rigid structure of HAP and strong interaction in PMo4V8/HAP (31) allowed this catalyst to be reused for at least six times with high stability and duration.

Marisic

, p. 2312,2314 (1940)

Oxidation of levulinic acid for the production of maleic anhydride: breathing new life into biochemicals

Chatzidimitriou, Anargyros,Bond, Jesse Q.

, p. 4367 - 4376 (2015)

Levulinic acid (LA) is a biomass-derived platform chemical that could play a central role in emerging industries as an intermediate that facilitates production of bio-based commodities. In this context, we present a novel, catalytic pathway for the synthesis of maleic anhydride (MA) via oxidative cleavage of the methyl carbon in LA over supported vanadates. The approach is demonstrated in a continuous flow, packed bed reactor, and we have observed that VOx supported on SiO2 achieves single-pass MA yields as high as 71%. Preliminary analysis suggests that LA might compete with butane as an industrial MA feedstock. Finally, bifunctional LA and monofunctional 2-pentanone display contrasting oxidative cleavage selectivities, indicating that methyl carbon cleavage during vapor phase oxidation over supported vanadates is unique to LA.

Catalytic aerobic oxidation of renewable furfural to maleic anhydride and furanone derivatives with their mechanistic studies

Lan, Jihong,Chen, Zhuqi,Lin, Jinchi,Yin, Guochuan

, p. 4351 - 4358 (2014)

Catalytic transformation of biomass-based furfural to value-added chemicals is an alternative route to the on-going fossil feedstock-based processes. This work describes catalytic aerobic oxidation of furfural to maleic anhydride, an important polymer starting material having a large market with H 5PV2Mo10O40 and Cu(CF 3SO3)2 catalysts. Under the optimized conditions, 54.0% yield of maleic anhydride can be achieved with about 7.5% yield of 5-acetoxyl-2(5H)-furanone formation. Notably, 5-acetoxyl-2(5H)-furanone is a highly value-added, biologically important intermediate that has been applied in pharmaceutical synthesis. The catalytic mechanism for furfural oxidation to maleic anhydride and 5-acetoxyl-2(5H)-furanone has been investigated in detail with identification of several key intermediates. the Partner Organisations 2014.

Maleic anhydride yield during cyclic n-butane/oxygen operation

Shekari, Ali,Patience, Gregory S.

, p. 334 - 338 (2010)

Cycling catalyst between a net oxidizing and reducing gaseous environment has been practiced commercially to produce maleic anhydride from n-butane over vanadium pyrophosphate. Typically, the oxidation period is less than 1 min to minimize catalyst inventory. In this study, the effect of the oxidation period on maleic anhydride productivity was assessed in the range of 0.3-10 min. Irrespective of the feed gas composition during the reduction period, the productivity increased linearly with the oxidation soak time in air. A full range of reducing conditions was examined from the pure redox mode (10% n-butane in argon) to highly oxidizing conditions typical of fixed bed operation (1.4% n-butane and 18.1% oxygen). On average, maleic anhydride yield increased by up to 50% when the oxidation time was extended from 0.3 to 10 min. The maleic anhydride yield was lowest under redox mode and it was highest when the feed composition was close to equimolar in n-butane (~6%) and oxygen. Our results show that industrial CFB reactor performance may be improved considerably by efficient regeneration of the catalyst and optimization of the reducing feed gas composition.

A comparison of the reactivity of "nonequilibrated" and "equilibrated" V-P-O catalysts: Structural evolution, surface characterization, and reactivity in the selective oxidation of n-butane and n-pentane

Albonetti,Cavani,Trifiro,Venturoli,Calestani,Lopez Granados,Fierro

, p. 52 - 64 (1996)

Changes occurring on thermal treatment of the precursor of vanadium/phosphorus mixed oxide, the industrial catalyst for the oxidation of n-butane, were studied. The precursor was mixed with stearic acid, used as an organic binder for pelletization of the powder. The calcination of the precursor leads to a partially oxidized compound, constituted of an amorphous VIV-P mixed oxide and a crystalline hydrated VV-P-O phase. The calcined compound, when left in a 1% hydrocarbon/air stream for 100 h leads to a "nonequilibrated" catalyst, and after 1000 h to the "equilibrated" catalyst. The catalytic activity of the nonequilibrated and equilibrated catalysts in n-butane and n-pentane oxidation was studied and compared; the chemical-physical features of the two catalysts were studied by means of XRD, FT-IR, chemical analysis, TGA, XPS, and TPD. Only well crystallized (VO)2P2O7 was detected in the equilibrated catalyst and a homogeneous distribution of surface centers seems to be present on its surface. In the case of nonequilibrated catalyst, a poorly crystallized (VO)2P2O7 is present together with an amorphous VIV-P-O phase and γ-VOPO4; these phases define a heterogeneous distribution of at least two kind of surface centers. This surface heterogeneity gives rise to a catalyst less selective in n-butane oxidation to maleic anhydride and less specific in the conversion of n-pentane to phthalic anhydride.

Promotion of V-P Oxide Catalyst for Butane Oxidation by Metal Additives

Tamaki, Jun,Morishita, Takehiro,Morishige, Hidetaka,Miura, Norio,Yamazoe, Noboru

, p. 13 - 16 (1992)

Mixed oxide catalyst V-P-O for the butane oxidation to maleic anhydride was significantly promoted by the addition of some metal cations.In paricular, the addition of a small amount of Bi (Bi/V = 0.02) was the most effective.Over the Bi-added catalyst, the MA selectiviy exceeded 70 molpercent up to the butane conversion level of 88 molpercent, attaining the maximum MA yield of 62 molpercent at 395 deg C.

-

Mason

, p. 700 (1930)

-

n-Butane Oxidation to Maleic Anhydride and Furan with no Carbon Oxide Formation using a Catalyst derived from VO(H2PO4)2

Sananes, Maria T.,Hutchings, Graham J.,Volta, Jean-Claude

, p. 243 - 244 (1995)

The oxidation of n-butane at 390 deg C over a catalyst derived from VO(H2PO4)2 gives only maleic anhydride and furan as products and no CO or CO2 are formed.

Atmospheric chemistry of benzene oxide/oxepin

Klotz, Bjoern,Barnes, Ian,Becker, Karl H.,Golding, Bernard T.

, p. 1507 - 1516 (1997)

The atmospheric chemistry of benzene oxide/oxepin, a possible intermediate in the atmospheric oxidation of aromatic hydrocarbons, has been investigated in a large volume photoreactor at 298 K and atmospheric pressure using in situ FTIR spectroscopy for the analysis. Rate coefficients of (10.0 ± 0.4) × 10-11 and (9.2 ± 0.3) × 10-12 cm3 molecule-1 s-1 have been determined for the reaction of benzene oxide/oxepin with OH and NO3 radicals, respectively. Reaction with OH radicals produces almost exclusively the (E,Z)- and (E,E)-isomers of hexa-2,4-dienedial, whereas reaction with NO3 produces (Z,Z)-hexa-2,4-dienedial and unidentified organic nitrates. Phenol has been observed as a major product of the thermal decomposition, visible and UV photolysis of benzene oxide/oxepin. The results are discussed in conjunction with the oxidation mechanisms of aromatic hydrocarbons. The major atmospheric sinks of benzene oxide/oxepin will be reaction with OH radicals and photolysis and, under smog chamber conditions with high NO2 concentrations, also reaction with NO3.

n-Butane oxidation using VO(H2PO4)2 as catalyst derived from an aldehyde/ketone based preparation method

Bartley,Rhodes,Kiely,Carley,Hutchings

, p. 4999 - 5006 (2000)

A detailed study of n-butane oxidation over vanadium phosphate catalysts derived from in situ activation of VO(H2PO4)2 is described and discussed. New methods of preparation of VO(H2PO4)2 are described using the reaction of V2O5 and H3PO4 or VOPO4 · 2H2O with an aldehyde or ketone as a reducing agent. It is proposed that the enol form of the aldehyde and ketone act as the reducing agent. VO(H2PO4)2 can also be obtained by reduction of VOPO4 phases with alcohols. The catalysts derived from VO(H2PO4)2 by in situ activation in 1.5% butane in air at 400 °C for 72 h are largely disordered and, by detailed powder X-ray diffraction and laser Raman spectroscopy, are shown to be comprised mainly of disordered material containing some untransformed VO(H2PO4)2, VOPO4 phases and possibly some VO(PO3)2. The catalysts derived from all the forms of VO(H2PO4)2 investigated are found to exhibit maleic anhydride selectivities in the range 20-30% and it is concluded that the low selectivity is due to the presence of VOPO4 phases in the activated catalysts.

Photocatalytic valorization of furfural to value-added chemicals via mesoporous carbon nitride: a possibility through a metal-free pathway

Battula, Venugopala R.,Chauhan, Deepak K.,Giri, Arkaprabha,Kailasam, Kamalakannan,Patra, Abhijit

, p. 144 - 153 (2022/01/19)

Strategizing the exploitation of renewable solar light could undoubtedly provide new insight into the field of biomass valorization. Therefore, for the first time, we reported a heterogeneous photocatalytic oxidation route of renewable furfural (FUR) to produce industrial feedstocks maleic anhydride (MAN) and 5-hydroxy-2(5H)-furanone (HFO) under simulated solar light (AM 1.5G) using molecular oxygen (O2) as a terminal oxidant and mesoporous graphitic carbon nitride (SGCN) as a photocatalyst. SGCN showed an excellent photoconversion (>95%) of FUR with 42% and 33% selectivity to MAN and HFO, respectively. Moreover, an excellent selectivity towards MAN (66%) under natural sunlight indicates a pioneering route for the sustainable production of MAN. In addition, the underlying mechanistic route of the FUR photo-oxidation was investigated via various experiments including scavenger studies, substrate studies, and electron spin resonance (ESR) studies which constructively proved the pivotal role of singlet oxygen (1O2) and holes (h+) in FUR photo-oxidation.

Highly Efficient Biobased Synthesis of Acrylic Acid

Feringa, Ben L.,Hermens, Johannes G. H.,Jensma, Andries

supporting information, (2021/12/16)

Petrochemical based polymers, paints and coatings are cornerstones of modern industry but our future sustainable society demands greener processes and renewable feedstock materials. A challenge is to access platform monomers from biomass resources while integrating the principles of green chemistry in their chemical synthesis. We present a synthesis route starting from biomass-derived furfural towards the commonly used monomers maleic anhydride and acrylic acid, implementing environmentally benign photooxygenation, aerobic oxidation and ethenolysis reactions. Maleic anhydride and acrylic acid, transformed into sodium acrylate, were isolated in yields of 85 % (2 steps) and 81 % (4 steps), respectively. With minimal waste and high atom efficiency, this biobased route provides a viable alternative to access key monomers.

Method for preparing maleic anhydride

-

Paragraph 0024-0041; 0044-0065, (2021/04/14)

The invention relates to a method for oxidizing biomass-based furan derivatives furfural and 5-hydroxymethyl furfural into maleic anhydride under photocatalysis of metal oxide or loaded metal oxide. According to the method, furfural or 5-hydroxymethyl furfural is used as a reaction substrate, oxygen is used as an oxidizing agent, metal oxide or loaded metal oxide is used as a catalyst, and selective oxidation of furfural or 5-hydroxymethyl furfural into maleic anhydride is realized under the irradiation of visible light of 400-650nm. The method comprises the following reaction processes: dissolving a substrate in a solvent, adding a catalyst, carrying out oxygen replacement and sealing on gas in a photoreactor, and carrying out a reaction at a reaction temperature of not more than 40 DEG C for not less than 0.5 h under irradiation of visible light of 400-650 nm to generate maleic anhydride. The synthesis method may have important application to preparation of maleic anhydride under mild conditions.

Insights into the catalytic mechanism of 5-hydroxymethfurfural to phthalic anhydride with MoO3/Cu(NO3)2in one-pot

Feng, Yunchao,Jia, Wenlong,Li, Weile,Lin, Lu,Sun, Yong,Tang, Xing,Zeng, Xianhai,Zhao, Xiaoyu,Zuo, Miao

, p. 5656 - 5662 (2021/08/24)

Recently, we reported a synthetic approach to obtain renewable phthalic anhydride (PA) from 5-hydroxymethfurfural (HMF) with a yield of 63.2% using MoO3/Cu(NO3)2 as a catalyst in one pot, for the first time. The reaction pathway has been elucidated in our previous study. Herein, the synergistic catalytic mechanism of MoO3/Cu(NO3)2 for the oxidation of HMF to PA was investigated. The commercially available MoO3 (c-MoO3) with superior characteristics, including more lattice oxygen and better oxygen-donating capacity, provides higher activity for the oxidation of HMF to PA. More importantly, the synergy between c-MoO3 and Cu(NO3)2 ensured the high yield of PA through the Mo6+/Mo4+ redox couple facilitated by the redox cycling of Cu2+/Cu+ with the assistance of oxygen.

Process route upstream and downstream products

Process route

3-bromodihydro-2,5-furandione
5470-44-0

3-bromodihydro-2,5-furandione

maleic anhydride
108-31-6

maleic anhydride

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

Conditions
Conditions Yield
Destillation;
maleic anhydride
108-31-6

maleic anhydride

acetic acid
64-19-7,77671-22-8

acetic acid

benzoic acid
65-85-0,8013-63-6

benzoic acid

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With δ-manganese oxide; oxygen; at 195 ℃; for 12h; Reagent/catalyst;
maleic anhydride
108-31-6

maleic anhydride

benzaldehyde
100-52-7

benzaldehyde

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
With vanadia; at 400 ℃; Air;
38.9%
9.6%
0.8%
at 300 ℃; Air;
2.7%
1.1%
0.9%
maleic anhydride
108-31-6

maleic anhydride

phthalic anhydride
85-44-9

phthalic anhydride

formic acid
64-18-6

formic acid

propane
74-98-6

propane

3-formyloxy-propene
1838-59-1

3-formyloxy-propene

allyl acrylate
999-55-3

allyl acrylate

benzaldehyde
100-52-7

benzaldehyde

acetic acid
64-19-7,77671-22-8

acetic acid

propionic acid
802294-64-0,79-09-4

propionic acid

acrylic acid
79-10-7

acrylic acid

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
With oxygen; at 270 ℃; under 1125.11 Torr; Product distribution / selectivity; Gas phase; Heterogeneous catalysis;
maleic anhydride
108-31-6

maleic anhydride

2-phenylacrolein
4432-63-7

2-phenylacrolein

benzaldehyde
100-52-7

benzaldehyde

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
With air; Mo-Te oxide; at 440 ℃; Product distribution; different catalysts and reaction temperatures;
48.5%
13.7%
2%
2%
maleic anhydride
108-31-6

maleic anhydride

carbon dioxide
124-38-9,18923-20-1

carbon dioxide

carbon monoxide
201230-82-2

carbon monoxide

benzaldehyde
100-52-7

benzaldehyde

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
With oxygen; vanadia; at 336.9 ℃; under 31.2 Torr; Mechanism; Product distribution; various pretreatments of catalyst, also supported catalysts, var. temperatures and partial pressures of oxygen;
maleic anhydride
108-31-6

maleic anhydride

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
With air; vanadia; titanium(IV) oxide; at 350 ℃; other catalysts, other toluene derivatives; var. temperature;
ethylbenzene
100-41-4,27536-89-6

ethylbenzene

maleic anhydride
108-31-6

maleic anhydride

benzaldehyde
100-52-7

benzaldehyde

benzoic acid
65-85-0,8013-63-6

benzoic acid

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
Conditions Yield
at 300 - 410 ℃;
C<sub>9</sub>H<sub>8</sub>O<sub>4</sub>

C9H8O4

2-methylfuran
534-22-5

2-methylfuran

maleic anhydride
108-31-6

maleic anhydride

Conditions
Conditions Yield
In neat (no solvent); at 20 ℃;

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  • Main Products:30
  • Country:China (Mainland)
  • Simagchem Corporation
  • Business Type:Manufacturers
  • Contact Tel:+86-592-2680277
  • Emails:sale@simagchem.com
  • Main Products:110
  • Country:China (Mainland)
  • Amadis Chemical Co., Ltd.
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-89925085
  • Emails:sales@amadischem.com
  • Main Products:29
  • Country:China (Mainland)
  • Wuhan Wonda Pharm Limited
  • Business Type:Lab/Research institutions
  • Contact Tel:027-84306245
  • Emails:wonda-chem@outlook.com
  • Main Products:30
  • Country:China (Mainland)
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