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108-31-6 Usage

Chemical Description

Maleic anhydride is an organic compound used in the production of polyester resins and other chemicals.

Chemical Description

Maleic anhydride is an organic compound with the formula C4H2O3.

Chemical Description

Maleic anhydride is an organic compound with a cyclic anhydride functional group.

Description

Maleic anhydride (MAN) is an organic compound with the chemical formula C4H2O3. It is the acid anhydride of maleic acid and in its pure state, it is a colorless or white solid with an acrid odor. Possessing two types of chemical functionality, maleic anhydride is a multifunctional chemical intermediate that is uniquely useful in chemical synthesis and applications.

Uses

Used in Chemical Synthesis:
Maleic anhydride is used as a dienophile in Diels-Alder syntheses, a widely employed method in organic chemistry for creating six-membered rings.
Used in Manufacturing Alkyd Resins:
Maleic anhydride is used in the production of alkyd-type resins, which are important in the formulation of coatings, inks, and adhesives.
Used in Dyestuff Industry:
It serves as a dye intermediate, contributing to the manufacturing process of various dyes.
Used in Pharmaceutical Industry:
Maleic anhydride is used in the production of pharmaceuticals, given its role as a key intermediate in the synthesis of several drugs.
Used in Agricultural Chemicals:
It is a precursor for the synthesis of agricultural chemicals such as maleic hydrazide and malathion, which are used in the production of herbicides and insecticides.
Used in Copolymerization Reactions:
Maleic anhydride is utilized in copolymerization reactions to produce a variety of polymers with specific properties.
Used in Unsaturated Polyester Resins (UPR) Production:
As a major end-use feedstock, maleic anhydride is used in the manufacture of unsaturated polyester resins, which have applications in construction, marine, and automobile industries.
Used in Synthetic Tensides, Insecticides, Herbicides, and Fungicides:
Maleic anhydride is employed in the synthesis of these substances for use in various industries.
Used in the Production of 1,4-Butanediol (BDO), Gamma-Butyrolactone, and Tetrahydrofuran (THF):
These chemicals are derived from maleic anhydride and have a wide range of applications, with BDO being one of the world's fastest-growing chemicals.
Physical Properties:
Maleic anhydride is a white, hydroscopic crystalline substance, often shipped as briquettes. It has an odor threshold concentration of 0.32 ppm and melts at 113°F. It is shipped both as a solid and in the molten state, and its vapors, fumes, and dusts can be strong irritants to the eyes, skin, and mucous membranes.
Chemical Properties:
In its pure form, maleic anhydride appears as colorless needles, white lumps, or pellets. It has an irritating, choking odor and dissolves in water to produce maleic acid. It also dissolves in ethanol and can produce esters.

Production Methods

Maleic anhydride was traditionally manufactured by the oxidation of benzene or other aromatic compounds. As of 2006, only a few smaller plants continue to use benzene; due to rising benzene prices, most maleic anhydride plants now use n-butane as a feedstock. In both cases, benzene and butane are fed into a stream of hot air, and the mixture is passed through a catalyst bed at high temperature. The ratio of air to hydrocarbon is controlled to prevent the mixture from catching on fire. Vanadium pentoxide and molybdenum trioxide are the catalysts used for the benzene route, whereas vanadium and phosphorus oxides are used for the butane route. 2 CH3CH2CH2CH3 + 7 O2 → 2 C2H2(CO)2O + 8 H2O.

Preparation

To a flask equipped with a Dean-Stark trap, condenser, and mechanical stirrer is added 116 gm (1.0 mole) of maleic acid and 120 ml of tetrachloroethane. The contents are heated, the water (18 ml, 1.0 mole) distilled off as the azeotrope, and the residue distilled under reduced pressure to afford 87.7 gm (89.5%) of the anhydride, b.p. 82-84°C (15 mm), m.p. 53°C. The residue remaining in the flask consists of about 10 gm of fumaric acid, m.p. 287°C. Fumaric and maleic acids both give maleic anhydride on heating. Fumaric acid must first be heated to a higher temperature to effect its conversion to maleic acid prior to its dehydration.

Reactions

The chemistry of maleic anhydride is very rich, reflecting its ready availability and bifunctional reactivity. It hydrolyzes, producing maleic acid, cis-HOOC–CH=CH–COOH. With alcohols, the halfester is generated, e.g., cis-HOOC–CH=CH–COOCH3. Maleic anhydride is a potent dienophile in Diels-Alder reactions. It is also a ligand for low-valent metal complexes, examples being Pt(PPh3)2(MA) and Fe(CO)4(MA). Maleic anhydride dimerizes in a photochemical reaction to form cyclo butane tetra carboxylic dianhydride (CBTA). This compound is used in the production of polyimides and as an alignment film for liquid crystal displays.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 6676, 1995 DOI: 10.1021/jo00126a013

Air & Water Reactions

Soluble in water. Reacts slowly with water to form maleic acid and heat.

Reactivity Profile

Maleic anhydride react vigorously on contact with oxidizing materials. Reacts exothermically with water or steam. Undergoes violent exothermic decomposition reactions, producing carbon dioxide, in the presence of strong bases (sodium hydroxide, potassium hydroxide, calcium hydroxide), alkali metals (lithium, sodium, potassium), aliphatic amines (dimethylamine, trimethylamine), aromatic amines (pyridine, quinoline) at temperatures above 150° C [Vogler, C. A. et al., J. Chem. Eng. Data, 1963, 8, p. 620]. A 0.1% solution of pyridine (or other tertiary amine) in Maleic anhydride at 185°C gives an exothermic decomposition with rapid evolution of gas [Chem Eng. News 42(8); 41 1964]. Maleic anhydride is known as an excellent dienophile in the Diels-Alder reaction to produce phthalate ester derivatives. These reactions can be extremely violent, as in the case of 1-methylsilacyclopentadiene [J. Organomet., Chem., 1979, 179, c19]. Maleic anhydride undergoes a potentially explosive exothermic Diels-Alder reaction with 1-methylsilacyclopenta-2,4-diene at 150C [Barton, T. J., J. Organomet. Chem., 1979, 179, C19], and is considered an excellent dieneophile for Diels-alder reactions [Felthouse, Timothy R. et al. "Maleic anhydride , Maleic Acid, and Fumaric Acid." Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. 2005].

Hazard

Irritant to tissue. Dermal and respiratory sensitization. Questionable carcinogen.

Health Hazard

Inhalation causes coughing, sneezing, throat irritation. Skin contact causes irritation and redness. Vapors cause severe eye irritation; photophobia and double vision may occur.

Fire Hazard

Behavior in Fire: When heated above 300°F in the presence of various materials may generate heat and carbon dioxide. Will explode if confined.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by ingestion and intraperitoneal routes. Moderately toxic by skin contact. A corrosive irritant to eyes, skin, and mucous membranes. Can cause pulmonary edema. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. A pesticide. Combustible when exposed to heat or flame; can react vigorously on contact with oxidizing materials. Explosive in the form of vapor when exposed to heat or flame. Reacts with water or steam to produce heat. Violent reaction with bases (e.g., sodmm hydroxide, potassium hydroxide, calcium hydroxide), dkah metals (e.g., sodium, potassium), amines (e.g., dimethylamine, triethylamine), lithium, pyridine. To fight fire, use alcohol foam. Incompatible with cations. When heated to decomposition (above 150℃) it emits acrid smoke and irritating fumes. See also ANHYDRIDES.

Potential Exposure

Maleic anhydride is used in unsaturated polyester resins; Agricultural chemical, and lubricating additives; in the manufacture of unsaturated polyester resins; in the manufacture of fumaric acid; in alkyd resin manufacture; in the manufacture of pesticides e.g., malathion, maleic hydrazide, and captan).

Shipping

UN2215 Maleic anhydride, Hazard class: 8; Labels: 8-Corrosive material. Maleic Anhydride is commercialized and transported in the solid and molten forms. The molten Maleic Anhydride is transported at temperatures ranging from 60 to 80°C in well-insulated tank containers or road tankers provided with heating devices. In the solid form, it can be transported as pastilles, which are usually packed in polyethylene bags of 25 kg and transported either by rail tanker or by truck.

Purification Methods

Crystallise it from *benzene, CHCl3, CH2Cl2 or CCl4. Sublime it under reduced pressure. [Skell et al. J Am Chem Soc 108 6300 1986, Beilstein 17 III/IV 5897, 17/11 V 55.]

Toxicity evaluation

Maleic anhydride was described as having anticarcinogenic properties, and some of the maleic copolymers can have biologic activity by themselves, especially antitumor activity. Information related to this compound is contradictory. Chromosomal aberrations in cultured hamster cells but no mutagenicity in in vitro tests in bacteria have been reported. No effects on cholinesterase activity have been described after exposure to maleic anhydride.

Incompatibilities

Reacts slowly with water (hydrolyzes) to form maleic acid, a medium-strong acid. Dust may form explosive mixture with air. Reacts with strong oxidizers, oil, water, alkali metals; strong acids; strong bases. Violent reaction with alkali metals and amines above 66C. Dangerous reaction with oxidizers, amines, alkali metals, and hydroxides. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic, and possibly flammable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur)

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal. Controlled incineration: care must be taken that complete oxidation to nontoxic products occurs.

Check Digit Verification of cas no

The CAS Registry Mumber 108-31-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 8 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 108-31:
(5*1)+(4*0)+(3*8)+(2*3)+(1*1)=36
36 % 10 = 6
So 108-31-6 is a valid CAS Registry Number.
InChI:InChI=1S/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H

108-31-6 Well-known Company Product Price

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  • TCI America

  • (M0005)  Maleic Anhydride  >99.0%(GC)(T)

  • 108-31-6

  • 25g

  • 105.00CNY

  • Detail
  • TCI America

  • (M0005)  Maleic Anhydride  >99.0%(GC)(T)

  • 108-31-6

  • 500g

  • 150.00CNY

  • Detail
  • Alfa Aesar

  • (A12178)  Maleic anhydride, 98+%   

  • 108-31-6

  • 250g

  • 183.0CNY

  • Detail
  • Alfa Aesar

  • (A12178)  Maleic anhydride, 98+%   

  • 108-31-6

  • 1000g

  • 234.0CNY

  • Detail
  • Alfa Aesar

  • (A12178)  Maleic anhydride, 98+%   

  • 108-31-6

  • 5000g

  • 756.0CNY

  • Detail
  • Aldrich

  • (M188)  Maleicanhydride  99%

  • 108-31-6

  • M188-25G-A

  • 441.09CNY

  • Detail
  • Aldrich

  • (M188)  Maleicanhydride  99%

  • 108-31-6

  • M188-1KG-A

  • 637.65CNY

  • Detail
  • Aldrich

  • (M188)  Maleicanhydride  99%

  • 108-31-6

  • M188-5KG-A

  • 848.25CNY

  • Detail
  • Aldrich

  • (M188)  Maleicanhydride  99%

  • 108-31-6

  • M188-25KG-A

  • 3,940.56CNY

  • Detail
  • Aldrich

  • (M625)  Maleicanhydride  powder, 95%

  • 108-31-6

  • M625-25G

  • 138.06CNY

  • Detail
  • Aldrich

  • (M625)  Maleicanhydride  powder, 95%

  • 108-31-6

  • M625-1KG

  • 1,478.88CNY

  • Detail
  • Sigma-Aldrich

  • (63200)  Maleicanhydride  puriss., ≥99.0% (NT)

  • 108-31-6

  • 63200-100G-F

  • 375.57CNY

  • Detail

108-31-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name maleic anhydride

1.2 Other means of identification

Product number -
Other names Toxilic anhydride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Maleic anhydride is used primarily in the formation of unsaturated polyester resins for use in boats, autos, trucks, buildings, piping, and electrical goods. Lube oil adhesives synthesized from maleic anhydride are used to prolong oil-change intervals and improve engine efficiency. Maleic anhydride is also used to make copolymers, pesticides, and other organic compounds, and in Diels-Alder syntheses.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:108-31-6 SDS

108-31-6Relevant articles and documents

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.

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 Raman spectroscopic investigation of surface redox mechanism of vanadyl pyrophosphate

Koyano, Gaku,Saito, Takaya,Misono, Makoto

, p. 415 - 416 (1997)

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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.

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. 2766,2767 (1979)

-

-

Varma,Saraf

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

-

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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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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Brown,Frozer

, p. 2917,2918 (1942)

Marisic

, p. 2312,2314 (1940)

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.

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.

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Mason

, p. 700 (1930)

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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.

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.

Endo Selectivity in the (4 + 3) Cycloaddition of Oxidopyridinium Ions

Fu, Chencheng,Harmata, Michael,Keto, Angus B.,Krenske, Elizabeth H.,Liu, Jinchu,Regalado, Erik L.,Roseli, Ras Baizureen,Sungnoi, Wanna,Wang, Heather

, p. 8302 - 8306 (2021/11/01)

The (4 + 3) cycloaddition of 2-trialkylsilyl-4-alkylbutadienes with an N-methyloxidopyridinium ion affords cycloadducts with high regioselectivity and excellent endo selectivity.

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