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Cas Database

108-30-5

108-30-5

Identification

  • Product Name:2,5-Furandione,dihydro-

  • CAS Number: 108-30-5

  • EINECS:203-570-0

  • Molecular Weight:100.074

  • Molecular Formula: C4H4O3

  • HS Code: Oral rat LD50: 1510 mg/kg

  • Mol File:108-30-5.mol

Synonyms:Succinicanhydride (8CI);2,5-Diketotetrahydrofuran;Butanedioic anhydride;Dihydro-2,5-furandione;NSC 8518;Rikacid SA;Succinic acid anhydride;Succinylanhydride;Succinyl oxide;Tetrahydro-2,5-dioxofuran;Tetrahydro-2,5-furandione;Succinic anhydride;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn,IrritantXi

  • Hazard Codes:Xi,Xn

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. 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. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. 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. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological 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

Supplier and reference price

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  • Manufacture/Brand:AK Scientific
  • Product Description:Succinic Anhydride
  • Packaging:25g
  • Price:$ 15
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  • Manufacture/Brand:AK Scientific
  • Product Description:Succinic Anhydride
  • Packaging:500g
  • Price:$ 54
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  • Manufacture/Brand:AK Scientific
  • Product Description:Succinic Anhydride
  • Packaging:5kg
  • Price:$ 317
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:Succinic anhydride, 99%
  • Packaging:5000g
  • Price:$ 175
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:Succinic anhydride, 99%
  • Packaging:250g
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:Succinic anhydride, 99%
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:Succinic anhydride, 99%
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  • Manufacture/Brand:Apolloscientific
  • Product Description:Succinic anhydride 97%
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  • Manufacture/Brand:Atlantic Research Chemicals
  • Product Description:Succinic Anhydride 95%
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  • Manufacture/Brand:Biorbyt Ltd
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Relevant articles and documentsAll total 129 Articles be found

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Hoffman,Schlessinger

, p. 1245 (1971)

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Photoinduced hydrometalation and hydrogenation of activated olefins with molybdenum and tungsten dihydrides (Cp2MH2)

Ko,Bookman,Kochi

, p. 1833 - 1842 (1990)

The early-transition-metal hydrides Cp2MoH2, Cp2WH2, and Cp2ReH rapidly form a series of electron donor-acceptor (EDA) complexes with various activated olefins as shown by the spontaneous appearance of vivid colors, the absorption energies of which correlate with the electron affinity of the olefinic acceptor and the oxidation (ionization) potential of the hydridometal donor in accord with Mulliken theory. Deliberate excitation of the charge-transfer absorption band leads to the quantitative hydrometalation of fumaronitrile by Cp2MoH2 at 25°C, and the structure of the σ hydrido alkyl adduct Cp2Mo(CHCNCH2CN)H (I) has been established by X-ray crystallography, (space group P21, monoclinic, with a = 8.090 (3) A?, b = 10.282 (4) A?, c = 8.316 (3) A?, β = 116.92 (3)°, V = 617 A?3, Z = 2, R = 0.028, Rw = 0.028 for 1802 reflections with I > 3σ having 2θ ≤ 60°). Under the same photochemical conditions, the tungsten analogue Cp2WH2 effects quantitative hydrogenation and leads to succinonitrile together with the olefinic π-adducts to tungstenocene in high yields. (In both cases, the thermal (dark) processes are nonexistent) The charge-transfer mechanism for olefin hydrometalation and hydrogenation stemming from charge separation in the EDA complex (i.e. [Cp2MH2?+,>C--C ?ox of the hydridometal species and the subsequent facile proton transfer from the labile cation radical Cp2MH2?+ (M = Mo, W) to the acceptor moiety. The close similarity of the photoinduced process for olefin hydrometalation and hydrogenation of various activated olefins with those effected thermally at higher temperatures is discussed.

Nickel promoted functionalization of CO2 to anhydrides and ketoacids

Greenburg, Zoe R.,Jin, Dong,Williard, Paul G.,Bernskoetter, Wesley H.

, p. 15990 - 15996 (2014)

The reductive functionalization of carbon dioxide into high value organics was accomplished via the coupling with carbon monoxide and ethylene/propylene at a zerovalent nickel species bearing the 2-((di-t-butylphosphino)methyl)pyridine ligand (PN). An initial oxidative coupling between carbon dioxide, olefin, and (PN)Ni(1,5-cyclooctadiene) afforded five-membered nickelacycle lactone species, which were produced with regioselective 1,2-coupling in the case of propylene. The propylene derived nickelacycle lactone was isolated and characterized by X-ray diffraction. Addition of carbon monoxide, or a combination of carbon monoxide and diethyl zinc to the nickelacycle lactone complexes afforded cyclic anhydrides and 1,4-ketoacids, respectively, in moderate to high yields. The primary organometallic product of the transformation was zerovalent (PN)Ni(CO)2. This journal is

Selective hydrogenation of maleic anhydride over Pd/Al2O3 catalysts prepared via colloid deposition

Yuan, Hongjing,Zhang, Chunlei,Huo, Weitao,Ning, Chunli,Tang, Yong,Zhang, Yi,Cong, Dequan,Zhang, Wenxiang,Luo, Jiahuan,Li, Su,Wang, Zhenlu

, p. 141 - 145 (2014)

Pd/Al2O3 catalysts were prepared via colloid deposition and the performance of the catalysts was examined in the selective hydrogenation of maleic anhydride to succinic anhydride. When the reaction was carried on in a batch system with 1,4-dioxane as the solvent (353 K and 1.0 MPa), high conversion of maleic anhydride (>98%) and high selectivity (>99%) for succinic anhydride were observed after 5 h. The as-prepared Pd/Al2O3 catalyst also showed excellent performance in solvent-free system and fixed-bed systems. The maleic anhydride (MA) conversion was greater than 98%, and high selectivity (>99%) for succinic anhydride was obtained after 1600 h in a fixed bed reacter. The results showed that the activity of the Pd/Al2O3 catalysts was excellent due to its high active surface area. [Figure not available: see fulltext.]

Heterogeneous catalysts for the cyclization of dicarboxylic acids to cyclic anhydrides as monomers for bioplastic production

Rashed, Md. N.,Siddiki,Ali, Md. A.,Moromi, Sondomoyee K.,Touchy, Abeda S.,Kon, Kenichi,Toyao, Takashi,Shimizu, Ken-Ichi

, p. 3238 - 3242 (2017)

Cyclic anhydrides, key intermediates of carbon-neutral and biodegradable polyesters, are currently produced from biomass-derived dicarboxylic acids by a high-cost multistep process. We present a new high-yielding process for the direct intramolecular dehydration of dicarboxylic acids using a reusable heterogeneous Lewis acid catalyst, Nb2O5·nH2O. Various dicarboxylic acids, which can be produced by a biorefinery process, are transformed into the corresponding cyclic anhydrides as monomers for polyester production. This method is suitable for the production of renewable polyesters in a biorefinery process.

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Knier,Hauke

, p. 3219 (1977)

-

-

Windholz,T.B.,Clements,J.B.

, p. 3021 - 3023 (1964)

-

-

Karger,M.H.,Mazur,Y.

, p. 528 - 531 (1971)

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Clay catalysis: A convenient and rapid formation of anhydride from carboxylic acid and isopropenyl acetate under microwave irradiation

Villemin,Labiad,Loupy

, p. 419 - 424 (1993)

The Montmorillonite KSF catalyses the synthesis of anhydrides from carboxylic acids in the presence of isopropenyl acetate under microwave irradiations.

Vanadium(v) oxoanions in basic water solution: A simple oxidative system for the one pot selective conversion of l-proline to pyrroline-2-carboxylate

Biancalana, Lorenzo,Tuci, Giada,Piccinelli, Fabio,Marchetti, Fabio,Bortoluzzi, Marco,Pampaloni, Guido

, p. 15059 - 15069 (2017)

The unprecedented, direct chemical oxidation of l-proline to pyrroline-2-carboxylate was achieved in water (pH 9-10) by means of NH4VO3/NH3 or V2O5/MOH (K = Na, K), and the anion was fully characterized as ammonium or alkaline metal salts. Quantitative yield and higher atom economy performance were achieved with the latter system, the alkaline salts being more stable than the ammonium one. Different mixed valence V(iv)/V(v) compounds precipitated from the reaction mixtures depending on the nature of the employed base. A possible reaction mechanism is proposed according to DFT calculations. The analogous reaction of trans-4-hydroxy-l-proline with NH4VO3/NH3 afforded pyrrole-2-carboxylic acid in 81% yield, while sarcosine underwent prevalent decomposition under similar experimental conditions. Instead, no reaction was observed with primary (glycine, l-alanine, l-phenylalanine) and tertiary α-amino acids (N,N-dimethyl-l-phenylalanine, N,N-dimethylglycine).

Mechanism of synthesis of maleic and succinic anhydrides by carbonylation of acetylene in solutions of palladium complexes

Bruk,Oshanina,Kozlova,Temkin,Odintsov

, p. 1071 - 1083 (1998)

The mechanism of synthesis of maleic and succinic anhydrides from acetylene and CO in the PdBr2 - LiBr - organic solvent catalytic system was studied using the procedure of advancement and discrimination of hypotheses. The hypotheses were obtained using the data bank on elementary steps and the Comb1 combinatorial program. The discrimination of the hypotheses was based on the data of NMR and IR spectroscopy, studies of isotope exchange, the role of potential organic intermediates, the kinetic isotope effect, and one-factor kinetic experiments. The most probable mechanism of synthesis of maleic anhydride includes insertion of acetylene and CO into the Pd - Pd bond of the Pd1 complex, which is formed from Pd11 at the initial step of the process. Succinic anhydride results from the intramolecular transformation of the hydride complex of palladium and maleic anhydride. The palladium hydride complexes detected in the contact solution apparently play the crucial role in the conjugation of oxidation, reduction, and addition type reactions.

Efficient cyclodehydration of dicarboxylic acids with oxalyl chloride

Kantin, Grigory,Chupakhin, Evgeny,Dar'in, Dmitry,Krasavin, Mikhail

, p. 3160 - 3163 (2017)

Literature examples illustrating the use of oxalyl chloride to prepare dicarboxylic acid anhydrides are surprisingly limited. At the same time, we have discovered a method involving the use of this readily available reagent which allowed the preparation of novel cyclic anhydrides where other, more conventional, methods had failed. Herein, we demonstrate that the method is applicable to a wide diversity of substrates, delivers good to excellent yields of cyclic anhydrides without chromatographic purification and can be considered a synthetic tool of choice whenever dicarboxylic acid cyclodehydration is required.

Gas-phase hydrogenation of maleic anhydride to γ-butyrolactone at atmospheric pressure over Cu-CeO2-Al2O3 catalyst

Yu, Yang,Guo, Yanglong,Zhan, Wangcheng,Guo, Yun,Wang, Yanqin,Wang, Yunsong,Zhang, Zhigang,Lu, Guanzhong

, p. 77 - 81 (2011)

Cu-CeO2-Al2O3 catalyst, prepared by co-precipitation method, was investigated for the gas-phase hydrogenation of maleic anhydride (MA) to γ-butyrolactone (GBL) at atmospheric pressure and the catalyst deactivation was also studied. Effects of catalyst composition, reaction temperature, and liquid hourly space velocity (LHSV) of raw material on the catalytic performance of Cu-CeO2-Al2O3 catalyst were investigated. The catalyst (molar ratio of Cu:Ce:Al = 1:1:2) showed better catalytic performance, in which both the conversion of MA and the selectivity of GBL kept 100% within two hours under the reaction conditions of 6 mL catalyst, 0.1 MPa, 220-280 °C, 30 mL min-1 H2, 0.6 h-1 LHSV of 20 wt.% MA/GBL. As for Cu-CeO2-Al 2O3 catalyst, smaller crystallite size of Cu and higher Cu surface area are favorable to increase its catalytic performance. The deactivation of Cu-CeO2-Al2O3 catalyst is due to formation of the compact wax-like deposition on the catalyst surface, which is probably ascribed to the strong adsorption of succinic anhydride and then polymerization on the catalyst surface. The catalytic performance of the regenerated catalyst can be recovered completely by the regeneration method of N2-air-H2 stage treatment.

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Brewster,Fusco

, p. 501 (1963)

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Ni/Al2O3 catalysts derived from spinel NiAl2O4 for low-temperature hydrogenation of maleic anhydride to succinic anhydride

Li, Jie,Ren, Yuanhang,Yue, Bin,He, Heyong

, p. 1166 - 1173 (2017)

Ni/Al2O3 catalysts were derived from spinel NiAl2O4 with different Ni content ((2.5, 5 and 7.5) wt%). The catalysts were obtained by H2 reduction and were investigated for the low-temperature hydrogenation of maleic anhydride (MA) to produce succinic anhydride (SA). The characterization results showed that Ni0 active sites were mainly derived during the H2 reduction from spinel NiAl2O4. Among the catalysts studied, employing the optimum preparation and reaction conditions with Ni(5%)/Al2O3 yielded the highest catalytic performance. A near-100% conversion of MA and ~90% selectivity to SA were achieved at 120 °C and 0.5 MPa of H2 with a weighted hourly space velocity (MA) of 2 h?1.

Pd/C modified with Sn catalyst for liquid-phase selective hydrogenation of maleic anhydride to gamma-butyrolactone

Li, Rongrong,Zhao, Jia,Han, Deman,Li, Xiaonian

, p. 1330 - 1335 (2017)

Pd catalysts suffered from poor selectivity and stability for liquid-phase hydrogenation of maleic anhydride (MA) to gamma-butyrolactone (GBL). Thus, Pd/C catalysts modified with different Sn loadings were synthesized, and characterized by XRD, XPS, TEM and elemental mapping. The types of alloy phase and the amounts of the surface Pd-SnOx sites altered along with Sn/Pd mass ratios from 0–1.0 synthesized in the process of preparation. The maximum reaction rate was 0.57?mol-GBL/(mol-Pd?min) and selectivity was 95.94% when the Sn/Pd mass ratio was 0.6. It might be attributed to the formation of Pd2Sn alloy and less amounts of Pd-SnOx sites.

Active ruthenium catalysts prepared by Cacumen Platycladi leaf extract for selective hydrogenation of maleic anhydride

Huang, Yangqiang,Ma, Yao,Cheng, Youwei,Wang, Lijun,Li, Xi

, p. 124 - 130 (2015)

Ruthenium-based catalysts were prepared by a biogenic method via Cacumen Platycladi leaf extract and tested in the liquid phase hydrogenation of maleic anhydride to the corresponding succinic anhydride. The reaction conditions were optimized by varying the Ru loading, reaction temperature, hydrogen pressure, reaction time and organic solvents to achieve the superb catalytic performance. Reusability tests and comparison with commercial catalysts were also studied on the biosynthesized Ru-based catalysts. Furthermore, a variety of characterization techniques, such as TEM, HRTEM, EDS and XPS showed the effectively introduction of ruthenium nanoparticles into the carbon supports. The analyses of FTIR and TG confirmed that the plant extract served as both reducing and protecting agents.

State of Palladium Complexes in the PdBr2–LiBr–CH3CN–H2O Catalytic System, Used to Obtain Succinic Anhydride

Putin, A. Yu.,Katsman,Bruk

, p. 222 - 230 (2019)

Abstract: UV–Vis spectroscopy is used to study the PdBr2–LiBr–CH3CN system at different concentrations of palladium and lithium bromides. The resulting data are mathematically processed using hypotheses that include the formation of monomeric and dimeric palladium complexes. Equilibrium constants of the stages of monomer and dimer complexation are calculated, along with the extinction coefficients of palladium complexes. The spectra of individual monomeric and dimeric palladium complexes are reproduced within the model, allowing for the formation of four monomeric and three dimeric complexes. UV–Vis and IR spectroscopy are used to analyze the state of palladium complexes in the PdBr2–LiBr–CH3CN system after contact with СО, and directly during the carbonylation of acetylene into succinic anhydride.

Continuous-Flow Production of Succinic Anhydrides via Catalytic β-Lactone Carbonylation by Co(CO)4?Cr-MIL-101

Park, Hoyoung D.,Dinca, Mircea,Román-Leshkov, Yuriy

, p. 10669 - 10672 (2018)

Industrial synthesis of succinic acid relies on hydrocarbon oxidation or biomass fermentation routes that suffer from energy-costly separation processes. Here we demonstrate an alternate route to succinic anhydrides via β-lactone carbonylation by heterogeneous bimetallic ion-pair catalysis in Co(CO)4--incorporated Cr-MIL-101 (Co(CO)4Cr-MIL-101, Cr-MIL-101 = Cr3O(BDC)3F, H2BDC = 1,4-benzenedicarboxylic acid). Postsynthetically introduced Co(CO)4- facilitates CO insertion to β-lactone substrates activated by the Lewis acidic Cr(III) centers of the metal-organic framework (MOF), leading to catalytic carbonylation with activity and selectivity profiles that compare favorably to those reported for homogeneous ion-pair catalysts. Moreover, the heterogeneous nature of the MOF catalyst enables continuous production of succinic anhydride through a packed bed reactor, with room temperature β-propiolactone carbonylation activity of 1300 molAnhydride·molCo-1 over 6 h on stream. Simple evaporation of the fully converted product stream yields the desired anhydride as isolated solids, highlighting the unique processing advantages conferred by this first example of heterogeneous β-lactone carbonylation pathway.

An Efficient One-Pot Synthesis of Bis Butenolides

Bayat, Mohammad,Fox, Joseph M.

, p. 1661 - 1664 (2016)

3,3′,4,4′-Tetramethyl-5,5′-dioxo-2,2′-bifuran-2,2′(5H,5′H) diyl diacetate was obtained from the reaction between 2,3-dimethyl maleic anhydride and acetic anhydride in the presence of zinc in toluene. This easy synthetic route gave bis butenolide in excellent yield.

A convenient method for synthesis of symmetrical acid anhydrides from carboxylic acids with trichloroacetonitrile and triphenylphosphine

Kim,Jang

, p. 395 - 399 (2001)

Various carboxylic acids are converted into the corresponding carboxylic acid anhydrides treated with trichloroacetonitrile and triphenylphosphine in the presence of triethylamine at room temperature.

Pyrene derived functionalized low molecular weight organic gelators and gels

Hahma, Arno,Bhat, Shreedhar,Leivo, Kimmo,Linnanto, Juha,Lahtinen, Manu,Rissanen, Kari

, p. 1438 - 1448 (2008)

Pyrene derived binary functionalized low molecular weight organic gelators (FLMOGs) and gels thereof in selected organic solvents were synthesized and characterized. The functionality refers to a functional group that does not take part in formation of the supramolecular gel network, but remains free and available for other purposes, such as to bind nanoparticles or other molecules into the gel structure. Functional groups were observed to disturb gel formation strongly, if they interact with each other within the same supramolecule due to the formation of competitive structures. Preventing such interactions restored the original gel properties. A gel with weaker supramolecular bonding than the binding between the functional groups was successfully made by separating the functional groups by distance. The π-π-interaction was found to be of negligible significance to the supramolecular binding energy, but probably essential to align the molecules to a one-dimensional chain and bring them into the range of van der Waals forces mainly responsible for the binding in this system. Solvent was observed to increase the binding energy of the supramolecule. All molecules were characterized by spectroscopic techniques and elemental analysis. Selected gels were characterized with rheometry, scanning electron microscopy, UV- and fluorescence spectroscopy. Gelation kinetics and hysteresis were measured by UV-spectroscopy and a fast gelation process was observed for all the gelators studied. The melting enthalpies were measured by DSC and calculated theoretically by PM3 level of theory. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Maleic anhydride hydrogenation to succinic anhydride over mesoporous Ni/TiO2 catalysts: Effects of Ni loading and temperature

Torres, Cecilia C.,Alderete, Joel B.,Mella, Claudio,Pawelec, Barbara

, p. 441 - 448 (2016)

Catalytic hydrogenation of maleic anhydride for the production of succinic anhydride can be a viable alternative to the higher energetic demand route based in the dehydration of succinic acid. In this sense, the metallic Ni catalysts supported on mesoporous TiO2 (anatase) substrate demonstrated to be very active and 100% selective in the liquid phase hydrogenation of maleic anhydride (MA) to succinic anhydride (SA). The catalysts, which were prepared via wet impregnation method with different Ni loading (5, 10 and 15?wt.%), were characterized by chemical analysis (ICP-AES), N2 physical adsorption-?desorption, H2-?temperature programmed reduction (H2-?TPR)?, X-ray diffraction (XRD)?, high resolution transmission electron spectroscopy (HR-TEM) and X-ray photoelectron spectroscopy (XPS). The Ni species interaction with support was investigated by TPR and by performing five catalyst recycling tests. After catalyst activation by reduction, the increase of Ni particle size with an increase of Ni loading was relatively small (from 6.9 to 8.9?nm) due to enhance of the metal-support interaction. After the first catalytic cycle, the optimized 5%Ni/TiO2 catalyst showed a small decrease in the Ni loading attributed to metal leaching during time course of reaction. Besides this, the 5%Ni/TiO2 catalyst exhibited a good stability during five continuous cycles with a very high yield of SA after 5 cycles. Finally, temperature experiments performed for the best system shown that the reaction temperature does not affect the SA selectivity in the temperature range studied (323?K–398?K).

Selective hydrogenation of maleic anhydride to succinic anhydride catalyzed by metallic nickel catalysts

Feng, Yonghai,Yin, Hengbo,Wang, Aili,Xie, Tao,Jiang, Tingshun

, p. 205 - 212 (2012)

Maleic anhydride was selectively hydrogenated to succinic anhydride over metallic nickel catalysts, such as Raney Ni and Ni nanoparticles, in liquid phase at reaction temperature lower than 130 °C. When the Raney Ni catalyst in solvents with different polarities catalyzed the hydrogenation of maleic anhydride to succinic anhydride, the solvent with high polarity favored the hydrogenation of maleic anhydride to succinic anhydride as compared to that with low polarity. When the hydrogenation reaction was catalyzed by Raney Ni catalyst at 100 °C and H2 pressure of 2.5 MPa for 360 min in acetic anhydride, the conversion of maleic anhydride and the selectivity of succinic anhydride were 99.6% and 100%, respectively. In solvent-free reaction system, γ-butyrolactone as a byproduct with the maximum selectivity of 14.8% was produced at 130 °C. All of the Ni nanoparticles with average diameters ranging from 8 to 313 nm showed higher catalytic activity than Raney Ni in liquid phase hydrogenation of maleic anhydride to succinic anhydride. When the Ni nanoparticles with an average diameter of 8 nm were used as the catalysts in the liquid phase hydrogenation at 80 °C and 2 MPa of H 2 for 150 min and the weight ratio of catalyst to maleic anhydride was 1:100, the conversion of maleic anhydride and the selectivity of succinic anhydride were 99.8% and 100%, respectively. The small particle size and the polycrystalline structure of Ni nanoparticles played important roles in the liquid phase selective hydrogenation of maleic anhydride to succinic anhydride.

NICKEL(0)-INDUZIERTE C-C-VERKNUEPFUNG ZWISCHEN KOHLENDIOXID UND ETHYLEN SOWIE MONO- ODER DI-SUBSTITUIERTEN ALKENEN

Hoberg, Heinz,Schaefer, Dietmar

, p. C51 - C53 (1983)

The nickel(0)-induced coupling of CO2 with ethylene or with mono- or di-substituted alkenes is described.The regioselectivity of this reaction has been determined.

-

Higuchi et al.

, p. 3001,3003,3004 (1967)

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New catalytic systems for oxidative carbonylation of acetylene to maleic anhydride

Bruk,Kozlova,Marshakha,Oshanina,Temkin,Kaliya

, p. 1875 - 1881 (1999)

A classification of polyfunctional catalytic systems based on discrimination of the main component (the catalyst participating in all stages of the formation of the product of catalytic reaction) and elucidating the functions of additional components of a catalytic system is suggested. The role of additional components in a number of new palladium-based catalytic systems used in the synthesis of maleic anhydride by oxidative carbonylation of acetylene was studied. It was established that the functions of Co and Fe phthalocyanine complexes (PcCo and Pc*Fe, respectively) in the mechanism of the process are different.

N, N′-Bis(trifluoromethanesulfonyl) Dicarboxylic Acid Amides

Belovezhets, L. A.,Shainyan, B. A.,Sterkhova, I. V.,Tolstikova, L. L.

, p. 63 - 67 (2020)

Glutaric, adipic, and sebacic acids reacted with 2 equiv of N-sulfinyltrifluoromethanesulfonamide in the presence of thionyl chloride as a catalyst to give the corresponding N, N′-bis(trifluoromethanesulfonyl) diamides. Under similar conditions, succinic and 4-nitrophthalic acids underwent dehydration to the corresponding anhydrides.

Selective liquid-phase hydrogenation of maleic anhydride to succinic anhydride on biosynthesized Ru-based catalysts

Ma, Yao,Huang, Yangqiang,Cheng, Youwei,Wang, Lijun,Li, Xi

, p. 40 - 44 (2014)

Ru-based catalysts, supported on activated carbon and carbon nanotubes, were synthesized by a simple and eco-friendly bioreduction method and tested in the liquid-phase hydrogenation of maleic anhydride. Over 2.0% Ru/AC, succinic anhydride was produced with a maximum yield of 99.2% without further hydrogenation to γ-butyrolactone. Well-defined spherical shapes with uniform small size of Ru nanoparticles and the residual plant biomass were responsible for the excellent catalytic activities and stabilities.

Selective hydrogenation of maleic anhydride to γ-butyrolactone over Pd/Al2O3 catalyst using supercritical CO2 as solvent

Pillai, Unnikrishnan R.,Sahle-Demessie, Endalkachew

, p. 422 - 423 (2002)

A selective hydrogenation of maleic anhydride to either γ-butyrolactone or succinic anhydride over simple Pd/Al2O3 catalyst under supercritical CO2 medium is described for the first time which has considerable promise for both lab-scale as well as industrial selective hydrogenations of low vapor pressure compounds without employing environmentally harmful organic solvents.

Quantitative Evaluation of the gem-Dimethyl Effect on the Succinic Acid Anhydride Equilibrium. Conformations of the Acids and Anhydrides by Empirical Force Field Calculations

Ivanov, Petko M.,Pojarlieff, Ivan G.

, p. 245 - 250 (1984)

In order to evaluate quantitatively the gem-dimethyl effect on the succinic acid anhydride equilibrium, the conformations of succinic acid and its 2-methyl-, racemic 2,3-dimethyl-, tetramethyl-, and racemic 2,3-di-t-butyl-derivatives have been calculated by means of Allinger's 1977 empirical force field.An extension of the field was developed to calculate the conformations of the respective anhydrides.The calculated preferred conformations compare well with existing experimental data.No low-energy hydrogen-bonded minima for the acids were obtained.Increased substitution in the acids caused conformational changes facilitating ring closure: smaller torsion angles of conformations with gauche carboxy groups, favourable bond length and angle deformations, and a reduced number of preferred conformations.In the anhydrides, substitution leads to a twist around the C(2)-C(3) bond of the ring.The ΔΔH values estimated for the diacid anhydride equilibria agree well with experimental data in water indicating that the main cause of the observed gem-dimethyl effect in the anhydrides is relief of intramolecular strain arising on substitution in the acids.

-

Anderson,R.J. et al.

, p. 3654 - 3655 (1974)

-

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Akimoto,Echigoya

, p. 278 (1973)

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Addition Reaction of Carboxylic Anhydrides to the Carbon-Nitrogen Double Bond of Unsubstituted Cyclic Imidates

Kobayashi, Shiro,Isobe, Michihisa,Saegusa, Takeo

, p. 1921 - 1925 (1982)

Acyclic and cyclic (SAn and GAn) carboxylic anhydrides were added at room temperature to the C=N bond of unsubstituted cyclic imidates of 2-oxazoline (OZO) and 5,6-dihydro-4H-1,3-oxazine (OZI) to give addition products quantitatively.In contrast to these findings, the reactions of acetyl halides with OZO and OZI yielded ring-opened products and the reactions of carboxylic anhydrides with 2-benzyl-2-oxazoline (BzOZO) afforded also the ring-opened products.The bicyclic addition product of OZO with SAn is equilibrated with a mixture of starting materials.The stereochemistry of addition products having a six-membered ring system is discussed.

Conversion of succinic acid over Ni and Co catalysts

Rojas, Mabel,Zarate, Ximena,Canales, Roberto I.,Dongil, Ana Belen,Pazo, Cesar,Saavedra-Torres, Mario,Escalona, Néstor

, p. 165 - 176 (2021)

Liquid-phase hydrogenation of succinic acid (SA) over supported Ni and Co catalysts was investigated at 200 °C and 6 MPa of H2. Reduced and passivated catalysts with the same surface metal density (2.5 atoms of metal per nm2 of support) were prepared by incipient wetness impregnation. The catalysts were characterized by X-ray diffraction (XRD), N2 adsorption, X-ray photoelectron spectroscopy (XPS), temperature-programmed reduction (TPR), CO-chemisorption, and temperature-programmed desorption of NH3 (TPD-NH3). The Ni and Co catalysts supported over SiO2 showed different product distribution, due to the adsorption of the SA over the surface of catalysts, determined by DFT calculations. The Co/SiO2, Co/SiO2-Al2O3, and Co/Al2O3 catalysts showed different product distribution, which was correlated with total acidity from TPD-NH3 results. In general, the Co catalysts promoted the hydrogenation process; however, the highest total acidity showed by Co/Al2O3 also promoted the dehydration process. Finally, the initial rate follows the trend according to the dispersion determined by CO-chemisorption.

CONFORMATION OF SUCCINIC ACID DERIVATIVES BY DOUBLE 13C-LABELLING

Menger, F.M.,Lee, L. H.

, p. 757 - 760 (1988)

Three-bonded carbon/carbon couplings (3Jcc) are used, in conjunction with MM2 calculations, to examine conformational equilibria in several di-13C-labelled succinic acid derivatives.

Rhodium-catalysed, Carbon Dioxide-mediated Aerobic Oxidation of Ethers

Fazlur-Rahman, A. K.,Tsai, Jing-Cherng,Nicholas, Kenneth M.

, p. 1334 - 1335 (1992)

In the presence of carbon dioxide (NBD = 2,5-norbornadiene) 1 catalyses the aerobic oxidation of ethers to esters with coproduction of formic acid.

On the Mechanism of the Homogeneous Catalytic Hydrogenation Using Anion-Promoted Metal Clusters

Zuffa, Janet L.,Gladfelter, Wayne L.

, p. 4669 - 4671 (1986)

-

Synthesis of succinic anhydride from maleic anhydride on Ni/diatomite catalysts

Guo, Shaofei,Shi, Li

, p. 137 - 141 (2013)

The characteristics and catalytic properties of Ni(5 wt%)/diatomite, Ni(5 wt%)/γ-Al2O3, Ni(5% wt)/Bentonite clay and Ni(5 wt%)/attapulgite clay were investigated and compared in terms of catalytic activities for liquid-phase hydrogenation of maleic anhydride (MA). The results showed that the diatomite support exhibited the highest activity and selectivity. Using Ni(7 wt%)/diatomite catalyst, the 100% conversion of MA and 96.20% selectivity to SA were obtained for MA hydrogenation at 190 C. The X-ray diffraction (XRD) studies showed that there is only NiO on the support and no elemental nickel (Ni0) and Ni2O3 was detected in unreduced samples. XRD and H2 temperature-programmed reduction (TPR) studies also showed that NiO species were all converted to metallic nickel (Ni0) after reduction at 350 C.

Preparation of Ni- or Pt-Containing Cyclic Esters by Oxidative Addition of Cyclic Carboxylic Anhydrides and Their Properties

Sano, Kenji,Yamamoto, Takakazu,Yamamoto, Akio

, p. 2741 - 2747 (1984)

Metal containing cyclic ester complexes, L (L=1,2-bis(diphenylphosphino)ethane (dpe) or 2,2'-bipyridine (bpy); R1, R2=H or CH3) and Ln )L=tricyclohexylphosphine (PCy3) or dpe; n=1 or 2), have been prepared by oxidative addition of cyclic carboxylic anhydrides to zero-valent metal complexes.These complexes have been characterized by elemental analysis and spectroscopies (IR as well as 1H-, 13C1H>-, and 31P1H>-NMR) and chemical rectivities.Rate of the oxidative addition of succinic anhydride to Ni(bpy)(cod) (cod=1,5-cyclooctadiene) is expressed by a second order rate equation, R=k, and temperature dependence of k gives the activation energy of 68 kJ mol-1.The reaction of methylsuccinic anhydride with Ni(cod)2 in the presence of tertiary phosphine or bpy affords two isomers, Ln and Ln, corresponding to two modes of C-O bond cleavage in methylsuccininc anhydride promoted by Ni; dependence of the ratio between the two isomers on the kind of ligand added and reaction conditions has been examined.

-

Froeschl,Maier

, p. 256,271, 272 (1932)

-

A Convenient Triphosgene-Mediated Synthesis of Symmetric Carboxylic Acid Anhydrides

Kocz, Remigiusz,Roestamadji, Juliatiek,Mobashery, Shahriar

, p. 2913 - 2914 (1994)

-

Hydrogenation of maleic anhydride to succinic anhydride over nickel/clay catalysts

Guo, Shaofei,Tian, Weiping,Shi, Li

, p. 757 - 763 (2012)

Hydrogenation of maleic anhydride (MA) to succinic anhydride (SA) over Ni/clay catalysts prepared by an impregnation method has been studied at different temperatures, Ni contents, pressures and weighted hourly space velocity (WHSV). The catalytic activity was greatly influenced by the temperature, Ni content, WHSV and pressure. A 97.1 % MA conversion with 99.6 % selectivity to SA was obtained over 5 %wt catalyst at 180 °C and at a pressure of 1 MPa H2. The catalysts were characterized by an array of techniques, including X-ray diffraction (XRD), H2 temperature-programmed reduction (TPR) and thermogravimetric analysis (TGA). XRD and TPR studies showed that nickel was present as Ni2? species on the support. Increasing the calcination temperature up to 650 °C led to the destruction of the support structure, as observed by TGA, while a calcination temperature of 550 °C gave the best results. Catalyst deactivation studies showed that the catalyst has a long lifetime, the yield of SA remaining better than 90 % even after a reaction time of 60 h. Studies on the catalyst induction showed that the presence or absence of an induction period was determined by the type of hydrogenation catalyst. Springer Science+Business Media Dordrecht 2012.

Selective gas-phase conversion of maleic anhydride to propionic acid on Pt-based catalysts

Regenhardt,Trasarti,Meyer,Garetto,Marchi

, p. 59 - 63 (2013)

Pt-based catalysts, supported on Al2O3, SiO 2 and SiO2-Al2O3, were prepared by incipient wetness impregnation and tested in the gas phase hydrogenation of maleic anhydride at atmospheric pressure and 240 C. In these conditions, the hydrogenolytic activity pattern was: Pt/SiO2 > Pt/Al 2O3 > Pt/SiO2-Al2O3, which is just the opposite of the support acidity trend. These metal Pt-based catalysts showed high selectivity to propionic acid, which was always higher than 80%. The selectivity pattern to this product was: Pt/Al2O 3 > Pt/SiO2 > Pt/SiO2-Al 2O3. Both activity and selectivity patterns may be explained on the basis of metal-support interaction and support acidity.

Carbon Dioxide as Modulator of the Oxidative Properties of Dioxygen in the Presence of Transition Metal Systems

Aresta, Michele,Fragale, Carlo,Quaranta, Eugenio,Tommasi, Immacolata

, p. 315 - 317 (1992)

In the presence of transition metal ( Fe, Rh) catalysts, CO2 can modulate the oxidative properties of O2 towards tetrahydrofuran (THF) and styrene; the intermediate formation of metal-peroxocarbonate species, , seems to play a key role in these processes.

Pd/BN catalysts for highly efficient hydrogenation of maleic anhydride to succinic anhydride

Cao, Zhou,Sheng, Guangzhe,Sun, Changyong,Wang, Jiandian,Xia, Wenjun,Xie, Xiaowei

, (2022/01/03)

A 0.33 wt% Pd/BN catalyst has been proved highly active for the liquid-phase selective hydrogenation of maleic anhydride (MA) to succinic anhydride (SA) at room temperature and highly selective to SA within a wide temperature range, far beyond the Pd/Al2O3 and Pd/MgO catalysts. An SA productivity of 6000 KgSA KgPd?1 h?1 and a high TOF value of 9.0 s?1 can be achieved at room temperature on the Pd/BN, and the high SA selectivity over 99.7% can be retained at the reaction temperature up to 150 oC. Detailed structural characterizations and reactant-adsorption/desorption tests have demonstrated that the support effect on MA hydrogenation is related not only to the adsorption configurations of MA on Pd, which exhibits the indirect effect of the support via the electronic interaction with Pd, but also to the direct adsorption of MA on the support itself. In particular, for our catalysts with the low Pd loading, the difference of metal centers is largely masked by the adsorption of the support itself. For the Pd/BN, the predominant MA adsorption on Pd through a di-σ mode, the weak MA adsorption with a small amount on BN, and a high H-spillover ability are responsible for its high activity and selectivity. Moreover, it has been also revealed that the catalyst prereduction temperature can change the catalytic performance of the Pd/BN through an integrated effect including the removal of residual chlorine on Pd and the growth of Pd particles.

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.

Application of two-dimensional MoS2 catalyst in catalyzing selective hydrogenation of maleic anhydride to prepare succinic anhydride

-

Paragraph 0033-0036; 0043-0060, (2021/06/21)

The invention relates to the field of catalysts, and particularly discloses application of a two-dimensional MoS2 catalyst in catalyzing selective hydrogenation of maleic anhydride to prepare succinic anhydride. A preparation method of the two-dimensional MoS2 catalyst comprises the following steps: mixing ammonium molybdate and thiourea in water, conducting reacting at 180-240 DEG C for 12-24 hours, collecting a product after the reaction is finished, conducting washing for multiple times, and conducting drying to obtain the two-dimensional MoS2 catalyst. The two-dimensional MoS2 catalyst provided by the invention has high conversion rate and high selectivity for preparing succinic anhydride by selective hydrogenation of maleic anhydride.

MENTHOL DERIVATIVE-CONTAINING COMPOSITION

-

Paragraph 0055, (2021/04/09)

PROBLEM TO BE SOLVED: To provide a menthol derivative-containing composition that suppresses a menthol-derived odor and sustains a refreshed feeling. SOLUTION: A composition contains (A) a menthol derivative or an alkali metal salt or an alkaline earth metal salt thereof, and (B) menthol or an alkali metal salt or an alkaline earth metal salt thereof. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Process route upstream and downstream products

Process route

2-bromomalonic acid
600-31-7

2-bromomalonic acid

thiophenol
108-98-5

thiophenol

succinic acid anhydride
108-30-5

succinic acid anhydride

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

hydrogen bromide

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
Conditions Yield
2-bromomalonic acid
600-31-7

2-bromomalonic acid

thiophenol
108-98-5

thiophenol

succinic acid anhydride
108-30-5

succinic acid anhydride

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

hydrogen bromide

diphenyldisulfane
882-33-7

diphenyldisulfane

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

carbon dioxide

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

4-butanolide
96-48-0

4-butanolide

succinic acid anhydride
108-30-5

succinic acid anhydride

formic acid
64-18-6

formic acid

Conditions
Conditions Yield
With (bis(1,2-diphenylphosphino)ethane)(2,5-norbornadiene)rhodium(I) tetrafluoroborate; oxygen; at 25 ℃; for 192h; under 2585.7 - 25857.4 Torr; other temp.; aerobic oxidation of other ethers;
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

4-butanolide
96-48-0

4-butanolide

succinic acid anhydride
108-30-5

succinic acid anhydride

butanedial
638-37-9

butanedial

Conditions
Conditions Yield
With FeCl2*THF; oxygen; for 0.5h; under 772.6 Torr; Product distribution; Ambient temperature; other methal complexes catalysts, other reagent (O2 + CO2) , also styrene;
carbon monoxide
201230-82-2

carbon monoxide

succinic acid anhydride
108-30-5

succinic acid anhydride

β-Propiolactone
57-57-8

β-Propiolactone

Conditions
Conditions Yield
Hexamethylbenzene; [(C1TPP)Al][Co(CO)4]; In tetrahydrofuran; at -78 - 60 ℃; for 3h; under 31029.7 Torr; Product distribution / selectivity; Molecular sieve; Inert atmosphere;
8%
88%
Hexamethylbenzene; [(C1TPP)Al][Co(CO)4]; In tetrahydrofuran; at -78 - 60 ℃; for 3h; under 31029.7 Torr; Product distribution / selectivity; Molecular sieve; Inert atmosphere;
13%
81%
With Hexamethylbenzene; [(tetra(4-chlorophenyl)porphyrinato)aluminium(III)][tetracarbonylcobaltate]; In tetrahydrofuran; at 60 ℃; for 3h; under 31029.7 Torr; Glovebox; Inert atmosphere;
88 %Spectr.
8 %Spectr.
carbon monoxide
201230-82-2

carbon monoxide

succinic acid anhydride
108-30-5

succinic acid anhydride

β-Propiolactone
57-57-8

β-Propiolactone

acetaldehyde
75-07-0,9002-91-9

acetaldehyde

Conditions
Conditions Yield
With [(tetra(4-chlorophenyl)porphyrinato)aluminium(III)bis(tetrahydrofuran)][tetracarbonylcobaltate]; at 80 ℃; for 4h; under 31029.7 Torr; Catalytic behavior; Glovebox; Inert atmosphere;
23.6 %Spectr.
50.8 %Spectr.
5.5 %Spectr.
succinic acid
110-15-6

succinic acid

succinic acid anhydride
108-30-5

succinic acid anhydride

4-Ketopimelic acid
502-50-1

4-Ketopimelic acid

Conditions
Conditions Yield
5-6 h Erhitzen der Schmelze; anschliessend Eindampfen mit konz. HCl;
1,3,5-Trioxan
110-88-3

1,3,5-Trioxan

Dimethyl succinate
106-65-0

Dimethyl succinate

succinic acid anhydride
108-30-5

succinic acid anhydride

methyl hydrogen succinate
3878-55-5

methyl hydrogen succinate

citraconic acid anhydride
616-02-4

citraconic acid anhydride

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

carbon dioxide

Conditions
Conditions Yield
With gamma-alumina; at 380 ℃; under 3750.38 Torr; Temperature; Pressure; Autoclave; Flow reactor;
26%
19%
8%
18%
1,3,5-Trioxan
110-88-3

1,3,5-Trioxan

methyl hydrogen succinate
3878-55-5

methyl hydrogen succinate

succinic acid anhydride
108-30-5

succinic acid anhydride

citraconic acid anhydride
616-02-4

citraconic acid anhydride

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

carbon dioxide

Dimethyl succinate
106-65-0

Dimethyl succinate

Conditions
Conditions Yield
With gamma-alumina; at 380 ℃; under 3750.38 Torr; Autoclave; Flow reactor;
23%
30%
15%
9%
Dimethyl succinate
106-65-0

Dimethyl succinate

succinic acid anhydride
108-30-5

succinic acid anhydride

methyl hydrogen succinate
3878-55-5

methyl hydrogen succinate

citraconic acid anhydride
616-02-4

citraconic acid anhydride

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

carbon dioxide

Conditions
Conditions Yield
With gamma-alumina; In methanol; water; at 380 ℃; under 3750.38 Torr; Concentration; Temperature; Kinetics; Autoclave; Flow reactor;
30%
18%
8%
10%

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