Welcome to LookChem.com Sign In|Join Free

Cas Database

110-17-8

110-17-8

Identification

Synonyms:2-Butenedioic acid (2E)- (9CI);2-Butenedioic acid (E)-;EPA Pesticide Chemical Code 051201;trans-Butenedioic acid;Allomaleic acid;Boletic acid;(E)-2-Butenedioic acid;1,2-Ethenedicarboxylic acid, trans-;2-(E)-Butenedioic acid;trans-2-Butenedioic acid;FumaricAcid;Fumaric acid (Tech and Food grade);L-Carnitine Fumaric Acid;1, 2-Ethenedicarboxylic acid, trans-;Fumaric acid (NF);2-Butenedioic acid, (E)-;Tumaric acid;Allomalenic acid;Butenedioic acid, (E)-;2-Butenedioic acid;USAF EK-P-583;(2E)-but-2-enedioic acid;Fumaric acid (8CI);Kyselina fumarova;Fumaric acid;

Post Buying Request Now
Entrust LookChem procurement to find high-quality suppliers faster

Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes: Xi:Irritant;

  • Signal Word:Warning

  • Hazard Statement:H319 Causes serious eye irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. In case of skin contact Rinse skin with plenty of water or shower. 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. Inhalation of dust may cause respiratory irritation. Compound is non-toxic when ingested. Prolonged contact with eyes or skin may cause irritation. (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 If material on fire or involved in fire: use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemicals, or carbon dioxide. Special Hazards of Combustion Products: Irritating fumes of maleic anhydride may form in fires. Behavior in Fire: Dust presents explosion hazard; knock down dust with water fog. (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: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Then store and dispose of according to local regulations. Environmental considerations - land spill: Dig a pit, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fiefighting water. Neutralize with agricultural lime (CaO), crushed limestone (CaCO3), or sodium bicarbonate (NaHCO3).

  • 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. Separated from oxidizing materials.The bulk material should be stored in a well-closed container in a cool, dry 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

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase

Relevant articles and documentsAll total 157 Articles be found

Production of Plant Phthalate and its Hydrogenated Derivative from Bio-Based Platform Chemicals

Lu, Rui,Lu, Fang,Si, Xiaoqin,Jiang, Huifang,Huang, Qianqian,Yu, Weiqiang,Kong, Xiangtao,Xu, Jie

, p. 1621 - 1627 (2018)

Direct transformation of bio-based platform chemicals into aromatic dicarboxylic acids and their derivatives, which are widely used for the manufacture of polymers, is of significant importance for the sustainable development of the plastics industry. However, limited successful chemical processes have been reported. This study concerns a sustainable route for the production of phthalate and its hydrogenated derivative from bio-based malic acid and erythritol. The key Diels–Alder reaction is applied to build a substituted cyclohexene structure. The dehydration reaction of malic acid affords fumaric acid with 96.6 % yield, which could be used as the dienophile, and 1,3-butadiene generated in situ through erythritol deoxydehydration serves as the diene. Starting from erythritol and dibutyl fumarate, a 74.3 % yield of dibutyl trans-4-cyclohexene-1,2-dicarboxylate is obtained. The palladium-catalyzed dehydrogenation of the cycloadduct gives a 77.8 % yield of dibutyl phthalate. Dibutyl trans-cyclohexane-1,2-dicarboxylate could be formed in nearly 100 % yield under mild conditions by hydrogenation of the cycloadduct. Furthermore, fumaric acid and fumarate, with trans configurations, were found to be better dienophiles for this Diels–Alder reaction than maleic acid and maleate, with cis configuration, based on the experimental and computational results. This new route will pave the way for the production of environmental friendly plastic materials from plants.

-

Rozelle,Alberty

, p. 1637 (1957)

-

Some aspects of the Knoevenagel-Doebner and Wittig reactions

Aparicio, F. J. Lopez,Herrera, F. J. Lopez

, p. C4 - C7 (1980)

-

Reid,Sack

, p. 1985,1987 (1951)

An efficient and practical system for the catalytic oxidation of alcohols, aldehydes, and α,β-unsaturated carboxylic acids

Grill, Joseph M.,Ogle, James W.,Miller, Stephen A.

, p. 9291 - 9296 (2006)

(Chemical Equation Presented) Upon exposure to commercial bleach (~5% aqueous sodium hypochlorite), nickel(II) chloride or nickel(II) acetate is transformed quantitatively into an insoluble nickel species, nickel oxide hydroxide. This material consists of high surface area nanoparticles (ca. 4 nm) and is a useful heterogeneous catalyst for the oxidation of many organic compounds. The oxidation of primary alcohols to carboxylic acids, secondary alcohols to ketones, aldehydes to carboxylic acids, and α,β- unsaturated carboxylic acids to epoxy acids is demonstrated using 2.5 mol % of nickel catalyst and commercial bleach as the terminal oxidant. We demonstrate the controlled and selective oxidation of several organic substrates using this system affording 70-95% isolated yields and 90-100% purity. In most cases, the oxidations can be performed without an organic solvent, making this approach attractive as a "greener" alternative to conventional oxidations.

TAN-1323 C and D, new concanamycin-group antibiotics; Detection of the angiostatic activity with a wide range of macrolide antibiotics

Ishii,Hida,Iinuma,Muroi,Nozaki

, p. 12 - 20 (1995)

We detected potent angiostatic activity in a MrOH extract from the mycelia of microbial strain S-45628 in the chick chorioallantoic membrane (CAM) assay. The producer was taxonomically characterized as Streptomyces purpurascens. Active principles designated TAN-1323 A~D were isolated and determined to be 18-membered macrolide antibiotics; components C and D are new members of this group, while components A and B are identical to concansmycins C and A, respectively. When tested in the CAM assay, components B and D gave huge avascular zones at the extremely low doses of 10~100ng/disk, although components A and C showed far weaker activity due to their preferential tissue-damaging effect on the CAM. The discovery that these 18-membered macrolide antibiotics are angiostatic substances prompted us to examine other types of macrolide antibiotics, leading to the discovery that 18-membered macrolide antibiotics such as bafilomycin C1, tylosin and leucomycin also show angiostatic activity on the CAM. Thus, angiostatic potential is widely distributed among macrolide antibiotics. The mechanism of action of these macrolide antibiotics is also discussed.

-

Butkewitsch

, p. 100,104 (1927)

-

Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling

Macegoniuk, Katarzyna,Kowalczyk, Rafa?,Rudzińska, Anna,Psurski, Mateusz,Wietrzyk, Joanna,Berlicki, ?ukasz

, p. 1346 - 1350 (2017)

Covalent enzyme inhibitors constitute a highly important group of biologically active compounds, with numerous drugs available on the market. Although the discovery of inhibitors of urease, a urea hydrolyzing enzyme crucial for the survival of some human pathogens, is a field of medicinal chemistry that has grown in recent years, covalent urease inhibitors have been rarely investigated until now. Forty Michael acceptor-type compounds were screened for their inhibitory activities against bacterial urease, and several structures exhibited high potency in the nanomolar range. The correlation between chemical reactivity towards thiols and inhibitory potency indicated the most valuable compound — acetylenedicarboxylic acid, with Ki?=42.5 nM and logkGSH=-2.14. Molecular modelling studies revealed that acetylenedicarboxylic acid is the first example of highly effective mode of binding based on simultaneous bonding to a cysteine residue and interaction with nickel ions present in the active site. Activity-reactivity profiling of reversible covalent enzyme inhibitors is a general method for the identification of valuable drug candidates.

Purification and characterization of a lyase from the EDTA-degrading bacterial strain DSM 9103 that catalyzes the splitting of [S,S]-ethylenediaminedisuccinate, a structural isomer of EDTA

Witschel, Margarete,Egli, Thomas

, p. 419 - 428 (1997)

The bacterial strain DSM 9103, able to utilize EDTA as a sole source of carbon, nitrogen, and energy, is also capable to grow with [S,S]-ethylenediaminedisuccinate ([S,S]-EDDS), a structural isomer of EDTA. In cell-free extracts of [S,S]-EDDS-grown bacteria, [S,S]-EDDS degradation was observed in the absence of any cofactors. An enzyme was purified 41-fold that catalyzed the non-hydrolytic splitting of [S,S]-EDDS leading to the formation of fumarate and N-(2-aminoethyl) aspartic acid. These data strongly suggest that the enzyme belongs to the group of carbon-nitrogen lyases. The splitting reaction was reversible, and an equilibrium constant of approximately 43.0 10-1 M was determined. Out of the three stereo-isomers of EDDS, [S,S]- and [R,S]-EDDS were accepted as substrates by the lyase, whereas [R,R]-EDDS remained unchanged in assays with both cell-free extracts and pure enzyme. The enzyme catalyzed the transformation of free [S,S]-EDDS and of [S,S]-EDDS-metal complexes with stability constant lower than 10, namely of MgEDDS, CaEDDS, BaEDDS and to a small extent also of MnEDDS; Fe(III)EDDS, NiEDDS, CuEDDS, CoEDDS and ZnEDDS were not transformed.

Structural and kinetic studies on adenylosuccinate lyase from Mycobacterium smegmatis and Mycobacterium tuberculosis provide new insights on the catalytic residues of the enzyme

Banerjee, Sanchari,Agrawal, Monika J.,Mishra, Diptimayee,Sharan, Siddharth,Balaram, Hemalatha,Savithri, Handanhal S.,Murthy, Mathur R. N.

, p. 1642 - 1658 (2014)

Adenylosuccinate lyase (ASL), an enzyme involved in purine biosynthesis, has been recognized as a drug target against microbial infections. In the present study, ASL from Mycobacterium smegmatis (MsASL) and Mycobacterium tuberculosis (MtbASL) were cloned, purified and crystallized. The X-ray crystal structure of MsASL was determined at a resolution of 2.16 A. It is the first report of an apo-ASL structure with a partially ordered active site C3 loop. Diffracting crystals of MtbASL could not be obtained and a model for its structure was derived using MsASL as a template. These structures suggest that His149 and either Lys285 or Ser279 of MsASL are the residues most likely to function as the catalytic acid and base, respectively. Most of the active site residues were found to be conserved, with the exception of Ser148 and Gly319 of MsASL. Ser148 is structurally equivalent to a threonine in most other ASLs. Gly319 is replaced by an arginine residue in most ASLs. The two enzymes were catalytically much less active compared to ASLs from other organisms. Arg319Gly substitution and reduced flexibility of the C3 loop might account for the low catalytic activity of mycobacterial ASLs. The low activity is consistent with the slow growth rate of Mycobacteria and their high GC containing genomes, as well as their dependence on other salvage pathways for the supply of purine nucleotides.

Microflow photochemistry - A reactor comparison study using the photochemical synthesis of terebic acid as a model reaction

Aida, Shin,Terao, Kimitada,Nishiyama, Yasuhiro,Kakiuchi, Kiyomi,Oelgem?ller, Michael

, p. 5578 - 5581 (2012)

The continuous-microflow photochemical synthesis of terebic acid from maleic acid was investigated in two different microreactor set-ups. The results were subsequently compared to analogue experiments in a conventional chamber reactor. Based on conversion rates, reactor design and energy efficiency calculations, the simple microcapillary reactor showed the best overall performance.

Mechanism of the Enzymic Elimination of Ammonia from 3-Substituted Aspartic Acids by 3-Methylaspartase

Botting, Nigel P.,Akhtar, Mahmoud,Cohen, Mark A.,Gani, David

, p. 1371 - 1373 (1987)

Kinetic experiments with 3-methylaspartase, using aspartic, 3-methylaspartic, and 3-ethylaspartic acid and the appropriate C-3 deuteriated isotopomers as substrates, reveal that C(3)-H bond cleavage is partially rate-limiting for 3-methylaspartic acid, much less rate-limiting for 3-ethylaspartic acid, and not rate-limiting at all for aspartic acid.

The 3-methylaspartase reaction probed using 2H- and 15N-Isotope effects for three substrates: A flip from a concerted to a carbocationic amino-enzyme elimination mechanism upon changing the C-3 stereochemistry in the substrate from R to S

Gani, David,Archer, Catherine H.,Botting, Nigel P.,Pollard, John R.

, p. 977 - 990 (1999)

The mechanisms of the elimination of ammonia from (2S,3S)-3-methylaspartic acid, (2S)-aspartic acid and (2S,3R)-3-methylaspartic acid, catalysed by the enzyme l-threo-3-methylaspartase ammonia-lyase (EC 4.3.1.2) have been probed using 15N-isotope effects. The 15N-isotope effects for V/K for both (2S,3S)-3-methylaspartic acid and aspartic acid are 1.0246±0.0013 and 1.0390±0.0031, respectively. The natural substrate, (2S,3S)-3-methylaspartic acid, is eliminated in a concerted fashion such that the C(β)-H and C(α)-N bonds are cleaved in the same transition state. (2S)-Aspartic acid appears to follow the same mechanistic pathway, but deprotonation of the conjugate acid of the base for C-3 is kinetically important and influences the extent of 15N-fractionation. (2S,3R)-3-Methylaspartic acid is deaminated via a stepwise carbocationic mechanism. Here we elaborate on the proposed model for the mechanism of methylaspartase and propose that a change in stereochemistry of the substrate induces a change in the mechanism of ammonia elimination. Copyright (C) 1999 Elsevier Science B.V.

ELIMINATION OF HYDROGEN FLUORIDE FROM FLUORINATED SUCCINIC ACIDS.(II) KINETICS OF DEHYDROFLUORINATION OF FLUORO-, 2,2-DIFLUORO-, MESO- AND DL-2,3-DIFLUORO-, AND TRIFLUOROSUCCINIC ACIDS

Hudlicky, M.,Glass, T. E.

, p. 15 - 28 (1983)

Elimination of hydrogen fluoride from fluorosuccinic acid gave fumaric acid, from 2,2-difluorosuccinic acid, meso- and DL-2,3-difluorosuccinic acid fluorofumaric acid, and dehydrofluorination of trifluorosuccinic acid afforded difluoromaleic acid.Kinetic data based on 1H NMR measurements are presented for temperatures of 60 deg C, 75 deg C and 90 deg C.All the dehydrofluorinations follow second order kinetics.Activation energies for the dehydrofluorination of the above acids were found to be: 19.3, 17.3, 18.8, 17.9 and 18.3 kcal, respectively.Since both diastereomeric 2,3-difluorosuccinic acids give fluorofumaric acid as the only product of dehydrofluorination, one of them (DL) undergoes trans elimination while the other (meso) must undergo cis elimination.

-

Herasymenko,Tyvonuk

, p. 78 (1930)

-

A new dipeptide antibiotic from Streptomyces collinus, Lindenbein.

Molloy,Lively,Gale,Gorman,Boeck

, p. 137 - 140 (1972)

-

On chemical reactions in the laser-induced breakdown of a liquid

Margulis,Ovchinnikov,Margulis

, p. 986 - 990 (2006)

It is shown experimentally that a laser-induced breakdown of a liquid is accompanied by chemical reactions initiated by radicals and excited species formed in the spark. It is found that, in water, the laser-induced breakdown is accompanied by the dissociation of water and dissolved nitrogen molecules with the formation of HNO2 and HNO3, while, in a FeSO 4 aqueous solution, by the Fe2+ → Fe3+ oxidation reaction. It is assumed that the mechanism of the process is analogous to that of the action of ionizing radiations and the chemical action of ultrasonically induced cavitation (it is proposed that this mechanism of chemical action of a laser-induced spark proposed be termed indirect). Energy yields of these reactions are found to be of the same order of magnitude as for sonochemical redox reactions. It is shown that the laser-induced breakdown of an aqueous solution of maleic acid is accompanied by its stereoisomerization into fumaric acid, a process catalyzed by small amounts of an alkyl bromide. It is established that, for the formation of fumaric acid in a laser-induced spark, the energy yield is about five orders of magnitude higher than that typical of the above-mentioned redox reactions in the laser-induced spark. Nauka/Interperiodica 2006.

Asymmetric Synthesis of (S)- and (R)-Malic Acid from Ketene and Chloral

Wynberg, Hans,Staring, Emiel G. J.

, p. 166 - 168 (1982)

Quinidine (5) catalyzes the addition of ketene (1) to chloral (2) at -50 deg C in toluene.The β-(trichloromethyl)-β-propiolactone 3 is formed virtually optically pure (98percent enantiomeric excess).A mechanism for this reaction, accounting for the high enantiomeric excess, is proposed.Known hydrolytic procedures convert the lactone 3 to malic acid (6).By proper choice of catalyst both (R)- and (S)-malic acid can be obtained optically pure.

N-terminal truncation of a maleate cis-trans isomerase from Rhodococcus jostii RHA1 results in a highly active enzyme for the biocatalytic production of fumaric acid

Liu, Xiangtao,Zhao, Qing,Ren, Jie,Dong, Wenyue,Wu, Qiaqing,Zhu, Dunming

, p. 44 - 50 (2013)

As part of the project to develop an efficient biocatalytic process for the production of fumaric acid, a full-length putative maleate cis-trans isomerase gene from Rhodococcus jostii RHA1 was synthesized and expressed in Escherichia coli Rosetta2 (DE3) pLysS, but the protein was not soluble and showed no catalytic activity. Bioinformatics analysis of the protein sequence indicated that there were two hydrophilic and two hydrophobic amino acid clusters in an alternate arrangement at the N-terminus, and 50 extra amino acid residues at the N-terminus were not present in the known maleate cis-trans isomerases. The alternate hydrophilic and hydrophobic clusters at the N-terminus were thus truncated one by one to evaluate their effect on the gene expression and enzyme activity. Three mutants (MaiR-D41/42-304AA, MaiR-D48/49-304AA and MaiR-D52/53-304AA) without the hydrophilic and hydrophobic clusters were expressed as soluble protein with maleate cis-trans isomerase activity. Among them, MaiR-D48 was purified and its properties were studied. The purified enzyme had a temperature optimum of 40 C and a wide pH range (5.0-9.0) with the optimum pH being 8.0. The whole cells of E. coli expressing MaiR-D48 catalyzed the isomerization of maleic acid to fumaric acid at 1 M substrate concentration, showing its potential for industrial use.

Mechanism of 3-methylaspartase probed using deuterium and solvent isotope effects and active-site directed reagents: Identification of an essential cysteine residue

Pollard, John R.,Richardson, Susan,Akhtar, Mahmoud,Lasry, Philippe,Neal, Tracy,Botting, Nigel P.,Gani, David

, p. 949 - 975 (1999)

The mechanism of the l-threo-3-methylaspartate ammonia-lyase (EC 4.3.1.2) reaction has been probed using deuterium and solvent isotope effects with three different substrates, (2S,3S)-3-methylaspartic acid, (2S)-aspartic acid and (2S,3R)-3-methylaspartic acid. Each substrate appears to form a covalent adduct with the enzyme through the amination of a dehydroalanine (DehydAla-173) residue. The true substrates are N-protonated and at low pH, the alkylammonium groups are deprotonated internally in a closed solvent-excluded pocket after K+ ion, an essential cofactor, has become bound to the enzyme. At high pH, the amino groups of the substrates are able to react with the dehydroalanine residue prior to K+ ion binding. This property of the system gives rise to complex kinetics at pH 9.0 or greater and causes the formation of dead-end complexes which lack Mg2+ ion, another essential cofactor. The enzyme-substrate adduct is subsequently deaminated in two elimination processes. Hydrazines act as alternative substrates in the reverse reaction direction in the presence of fumaric acid derivatives, but cause irreversible inhibition in their absence. Borohydride and cyanide are not inhibitors. N-Ethylmaleimide also irreversibly inactivates the enzyme and labels residue Cys-361. The inactivation process is enhanced in the presence of cofactor Mg2+ ions and Cys-361 appears to serve as a base for the removal of the C-3 proton from the natural substrate, (2S,3S)-3-methylaspartic acid. The dehydroalanine residue appears to be protected in the resting form of the enzyme by generation of an internal thioether cross-link. The binding of the substrate and K+ ion appear to cause a conformational change which requires hydroxide ion. This is linked to reversal of the thioether protection step and generation of the base for substrate deprotonation at C-3. The deamination reaction displays high reverse reaction commitments and independent evidence from primary deuterium isotope effect data indicates that a thiolate acts as the base for deprotonation at C-3. Copyright (C) 1999 Published by Elsevier Science Ltd.

-

Ssadikow

, p. 504,508 (1923)

-

Poly (4-vinylpyridine) catalyzed isomerization of maleic acid to fumaric acid

Li, Qiang,Tao, Weihua,Li, Aimin,Zhou, Qing,Shuang, Chendong

, p. 148 - 153 (2014)

Fumaric acid is an important industrial intermediate compound that is mostly produced by isomerization of maleic acid under the catalysis of thiourea. In this study, a solid catalyst, poly (4-vinylpyridine) resin, was firstly used instead of thiourea for the catalytic isomerization of maleic acid because of its ease of separation and reusability. A high isomerization conversion rate of 86% was obtained for 100 mL of 200 mg/L maleic acid solution with resin dosage of 0.1 g under 353 K. This high isomerization conversion was due to the high nucleophilicity of PVP molecules. The optimum pH of 1.5 was determined by the degree of ionization of maleic acid. In the kinetics study, the conversion of maleic acid exhibited a second-order kinetic equation with apparent activation energy of 226.06 kJ/mol. Furthermore, the regenerated resin demonstrated no loss of catalytic activity. The excellent catalytic performance and high recyclability suggest that PVP resin has promising application in the isomerization of maleic acid to fumaric acid.

Study on the Isomerization of Maleic Acid to Fumaric Acid without Catalyst

Gao, Zhuo,Chen, Wangmi,Chen, Xiaoting,Wang, Dali,Yi, Shouzhi

, p. 920 - 924 (2018)

Fumaric acid is an important food additive and industrial intermediate compound. The traditional methods of producing fumaric acid were catalyzed by maleic acid isomerization. In this study, isomerization of maleic acid in water without catalyst was inves

The Structure of Chalybaeizanic Acid and Quaesitic Acid, Two New Lichen Depsidones Related to Salazinic Acid

Elix, John A.,Wardlaw, Judith H.

, p. 713 - 716 (1999)

The depsidones chalybaeizanic acid (1,4,10-trihydroxy-8-methyl-3,7-dioxo-1,3-dihydro-7H-isobenzofuro[4,5-b][1,4]benzodioxepin-5,11-dicarbaldehyde) (4) and quaesitic acid (11-formyl-1,4,10-trihydroxy-8-methyl-3,7-dioxo-1,3-dihydro-7H-isobenzofuro[4,5-b][1,4]benzodioxepin-5-methyl hydrogen fumarate) (5) have been isolated from the lichens Xanthoparmelia amphianthoides and Hypotrachyna quaesita respectively, and their structures determined by a combination of spectroscopic evidence, partial synthesis, derivatization or degradation reactions.

-

Ikutani,Y.

, p. 3602 - 3603 (1970)

-

-

Tilden,Marshall

, p. 494 (1895)

-

Oxidation of aliphatic side chains in anthracene Diels-Alder adducts

McCormick, Frankie A.,Marquardt, Donald J.

, p. 5169 - 5172 (1994)

An efficient oxidation of methyl and primary side chains of anthracene Diels Alder adducts with KMnO4 is reported. The oxidation leaves the bridgehead methines intact providing Diels-Alder adducts of anthracenecarboxylic acids. Retro Diels-Alder reaction allows for the preparation of the parent anthracenecarboxylic acids.

A covalent succinylcysteine-like intermediate in the enzyme-catalyzed transformation of maleate to fumarate by maleate isomerase

Fisch, Florian,Fleites, Carlos Martinez,Delenne, Marie,Baudendistel, Nina,Hauer, Bernhard,Turkenburg, Johan P.,Hart, Sam,Bruce, Neil C.,Grogan, Gideon

, p. 11455 - 11457 (2010)

Maleate isomerase (MI), a member of the Asp/Glu racemase superfamily, catalyzes cis-trans isomerization of the C2-C3 double bond in maleate to yield fumarate. Mutational studies, in conjunction with the structure of the C194A mutant of Nocardia farcinica MI cocrystallized with maleate, have revealed an unprecedented mode of catalysis for the superfamily in which the isomerization reaction is initiated by nucleophilic attack of cysteine at the double bond, yielding a covalent succinylcysteine-like intermediate.

Purification and characterization of fumarase from Corynebacterium glutamicum

Genda, Tomoko,Watabe, Shoji,Ozaki, Hachiro

, p. 1102 - 1109 (2006)

Fumarase (EC 4.2.1.2) from Corynebacterium glutamicum (Brevibacterium flavum) ATCC 14067 was purified to homogeneity. Its amino-terminal sequence (residues 1 to 30) corresponded to the sequence (residues 6 to 35) of the deduced product of the fumarase gene of C. glutamicum (GenBank accession no. BAB98403). The molecular mass of the native enzyme was 200 kDa. The protein was a homotetramer, with a 50-kDa subunit molecular mass. The homotetrameric and stable properties indicated that the enzyme belongs to a family of Class II fumarase. Equilibrium constants (Keq) for the enzyme reaction were determined at pH 6.0, 7.0, and 8.0, resulting in Keq = 6.4, 6.1, and 4.6 respectively in phosphate buffer and in 16, 19, and 17 in non-phosphate buffers. Among the amino acids and nucleotides tested, ATP inhibited the enzyme competitively, or in mixed-type, depending on the buffer. Substrate analogs, meso-tartrate, D-tartrate, and pyromellitate, inhibited the enzyme competitively, and D-malate in mixed-type.

-

Davies,Evans

, p. 74,77 (1956)

-

-

Taube, H.

, p. 526 - 531 (1943)

-

Foster et al.

, p. 663,667 (1949)

Pompon Dahlia-like Cu2O/rGO Nanostructures for Visible Light Photocatalytic H2 Production and 4-Chlorophenol Degradation

Karthikeyan, Sekar,Ahmed, Kassam,Osatiashtiani, Amin,Lee, Adam F.,Wilson, Karen,Sasaki, Keiko,Coulson, Ben,Swansborough-Aston, Will,Douthwaite, Richard E.,Li, Wei

, p. 1699 - 1709 (2020)

Hierarchical Cu2O nanospheres with a Pompon Dahlia-like morphology were prepared by a one-pot synthesis employing electrostatic self-assembly. Nanocomposite analogues were also prepared in the presence of reduced graphene oxide (rGO). Photophysical properties of the hierarchical Cu2O nanospheres and Cu2O/rGO nanocomposite were determined, and their photocatalytic applications evaluated for photocatalytic 4-chlorophenol (4-CP) degradation and H2 production. Introduction of trace (2O for H2 production from 2.23 % to 3.35 %, giving an increase of evolution rate from 234 μmol.g?1.h?1 to 352 μmol.g?1.h?1 respectively. The AQE for 4-CP degradation also increases from 52 % to 59 %, with the removal efficiency reaching 95 % of 10 ppm 4-CP within 1 h. Superior performance of the hierarchical Cu2O/rGO nanocomposite is attributable to increased visible light absorption, reflected in a greater photocurrent density. Excellent catalyst photostability for >6 h continuous reaction is observed.

-

Owen,Simonsen

, (1933)

-

Characterization of the cross-linked structure of fumarate-based degradable polymer networks

Timmer, Mark D.,Jo, Seongbong,Wang, Chuanyue,Ambrose, Catherine G.,Mikos, Antonios G.

, p. 4373 - 4379 (2002)

A new method was developed to examine networks formed with linear macromers of fumaric acid and diacrylate cross-linking agents in order to analyze their cross-linked structure. This method involved the accelerated degradation of the networks and the analysis of the degradation products. Two model networks of poly(propylene fumarate) (PPF) cross-linked with poly(propylene fumarate)-diacrylate (PPF-DA) and oligo(poly(ethylene glycol) fumarate) (OPF) cross-linked with poly(ethylene glycol)-diacrylate (PEG-DA) were evaluated with this method to determine the macromer and cross-linking agent conversions, the network cross-linking density, and an estimate of the molecular weight between crosslinks. The validity of the method was confirmed by the analysis of the composition of the un-cross-linked macromers and the correlation of the mechanical properties of the cross-linked polymers with the macromer/cross-linking agent double bond ratio. The results showed that acrylate species had participated more than fumarates in network formation. Furthermore, the structure of PPF/PPF-DA networks was influenced by the amount of cross-linking agent in the polymer formulation, and the OPF/PEG-DA network structure was controlled by the number of repeating fumarate units in the macromer. This method provides a new means to characterize the macromolecular structure of fumarate-based networks.

Size-Dependent Visible Light Photocatalytic Performance of Cu2O Nanocubes

Karthikeyan, Sekar,Kumar, Santosh,Durndell, Lee J.,Isaacs, Mark A.,Parlett, Christopher M. A.,Coulson, Ben,Douthwaite, Richard E.,Jiang, Zhi,Wilson, Karen,Lee, Adam F.

, p. 3554 - 3563 (2018)

Well-defined Cu2O nanocubes with tunable dimensions and physicochemical properties have been prepared using a simple one-pot reaction. Reduction of Cu(II) salts by ascorbic acid in the presence of PEG as a structure-directing agent affords crystalline Cu2O nanocubes of between 50 to 500 nm. Optical band gap, band energies, charge-carrier lifetimes and surface oxidation state systematically evolve with nanocube size, and correlate well with visible light photocatalytic activity for aqueous phase phenol degradation and H2 production which are both directly proportional to size (doubling between 50 and 500 nm). HPLC reveals fumaric acid as the primary organic product of phenol degradation, and selectivity increases with nanocube size at the expense of toxic catechol. Apparent quantum efficiencies reach 26 % for phenol photodegradation and 1.2 % for H2 production using 500 nm Cu2O cubes.

Ionic liquids breakdown by Fenton oxidation

Munoz, Macarena,Domínguez, Carmen M.,De Pedro, Zahara M.,Quintanilla, Asunción,Casas, Jose A.,Rodriguez, Juan J.

, p. 16 - 21 (2015)

Fenton oxidation has proved to be an efficient treatment for the degradation of ionic liquids (ILs) of different families viz. imidazolium, pyridinium, ammonium and phosphonium, in water. The intensification of the process, defined as the improvement on the efficiency of H2O2 consumption, by increasing the temperature is necessary to avoid high reaction times and the need of large excess of H2O2. In this work, temperatures within the range of 70-90°C have been used, which allowed an effective breakdown of the ILs tested (1 g L-1 initial concentration) with the stoichiometric amount of H2O2 and a relatively low Fe3+dose (50 mg L-1). Under these conditions conversion of the ILs was achieved in less than 10 min, with TOC reductions higher than 60% upon 4 h reaction time, except for the phosphonium IL. The remaining TOC corresponded mainly to short-chain organic acids. The treatment reduced substantially the ecotoxicity up to final values below 0.01 TU in most cases and a significant improvement of the biodegradability was achieved. Upon Fenton oxidation of the four ILs tested hydroxylated compounds of higher molecular weight than the starting ILs, fragments of ILs partially oxidized and short-chain organic acids were identified as reaction by-products. Reaction pathways are proposed.

-

Gelles,Pitzer

, p. 1974,1975, 1976 (1955)

-

Dittmar

, p. 2747 (1930)

Ordered mesoporous carbon as an efficient heterogeneous catalyst to activate peroxydisulfate for degradation of sulfadiazine

Cao, Di,Chen, Fan,Cheng, Hao,Huang, Cong,Li, Zhi-Ling,Liang, Bin,Nan, Jun,Sun, Kai,Wang, Ai-Jie

supporting information, (2022/01/26)

Catalytic potential of carbon nanomaterials in peroxydisulfate (PDS) advanced oxidation systems for degradation of antibiotics remains poorly understood. This study revealed ordered mesoporous carbon (type CMK) acted as a superior catalyst for heterogeneous degradation of sulfadiazine (SDZ) in PDS system, with a first-order reaction kinetic constant (k) and total organic carbon (TOC) mineralization efficiency of 0.06 min?1 and 59.67% ± 3.4% within 60 min, respectively. CMK catalyzed PDS system exhibited high degradation efficiencies of five other sulfonamides and three other types of antibiotics, verifying the broad-degradation capacity of antibiotics. Under neutral pH conditions, the optimal catalytic parameters were an initial SDZ concentration of 44.0 mg/L, CMK dosage of 0.07 g/L, and PDS dosage of 5.44 mmol/L, respectively. X-ray photoelectron spectroscopy and Raman spectrum analysis confirmed that the defect structure at edge of CMK and oxygen-containing functional groups on surface of CMK were major active sites, contributing to the high catalytic activity. Free radical quenching analysis revealed that both SO4?? and ?OH were generated and participated in catalytic reaction. In addition, direct electron transfer by CMK to activate PDS also occurred, further promoting catalytic performance. Configuration of SDZ molecule was optimized using density functional theory, and the possible reaction sites in SDZ molecule were calculated using Fukui function. Combining ultra-high-performance liquid chromatography (UPLC)–mass spectrometry (MS)/MS analysis, three potential degradation pathways were proposed, including the direct removal of SO2 molecules, the 14S-17 N fracture, and the 19C-20 N and 19C-27 N cleavage of the SDZ molecule. The study demonstrated that ordered mesoporous carbon could work as a feasible catalytic material for PDS advanced oxidation during removal of antibiotics from wastewater.

Preparation method of fumaric acid

-

Paragraph 0031-0095, (2021/06/22)

The invention discloses a preparation method of fumaric acid. The preparation method is characterized in that malic acid is used as a raw material, and under a solvent-free condition or in a hydrocarbon medium, malic acid is catalyzed to undergo a dehydration reaction so as to generate fumaric acid. The preparation method provided by the invention is simple in reaction process, and the key raw material malic acid can be obtained by fermenting biomass, so the preparation method is a supplement to a existing production route and relieve dependence on fossil resources; and besides, compared with a traditional fumaric acid production method, the method of the invention has the advantages that the use of high-pollution catalysts such as thiourea and oxybromide is avoided, and the method is green and safe since a dehydration reaction can be carried out under a normal-pressure condition. A catalyst used in the invention and a reaction process thereof are efficient and clean.

Preparation method of succinic acid

-

Paragraph 0028-0076, (2021/06/22)

The invention discloses a preparation method of succinic acid. The preparation method comprises the following step: with malic acid as a raw material, carrying out one-step reaction in a hydrogen atmosphere in the presence or absence of a non-polar medium and under the action of a metal-solid acid bifunctional catalyst to obtain succinic acid. In the preparation method, the above raw materials can be derived from biomass resources, so dependence on petroleum resources is reduced. By controlling process conditions, succinic acid can be obtained with high yield. The preparation method is simple in process and mild in conditions.

Biosynthesis ofl-alanine fromcis-butenedioic anhydride catalyzed by a triple-enzyme cascadeviaa genetically modified strain

Cui, Ruizhi,Liu, Zhongmei,Yu, Puyi,Zhou, Li,Zhou, Zhemin

, p. 7290 - 7298 (2021/09/28)

In industry,l-alanine is biosynthesized using fermentation methods or catalyzed froml-aspartic acid by aspartate β-decarboxylase (ASD). In this study, a triple-enzyme system was developed to biosynthesizel-alanine fromcis-butenedioic anhydride, which was cost-efficient and could overcome the shortcomings of fermentation. Maleic acid formed bycis-butenedioic anhydride dissolving in water was transformed tol-alanineviafumaric acid andl-asparagic acid catalyzed by maleate isomerase (MaiA), aspartase (AspA) and ASD, respectively. The enzymatic properties of ASD from different origins were investigated and compared, as ASD was the key enzyme of the triple-enzyme cascade. Based on cofactor dependence and cooperation with the other two enzymes, a suitable ASD was chosen. Two of the three enzymes, MaiA and ASD, were recombinant enzymes cloned into a dual-promoter plasmid for overexpression; another enzyme, AspA, was the genomic enzyme of the host cell, in which AspA was enhanced by a T7promoter. Two fumarases in the host cell genome were deleted to improve the utilization of the intermediate fumaric acid. The conversion of whole-cell catalysis achieved 94.9% in 6 h, and the productivity given in our system was 28.2 g (L h)?1, which was higher than the productivity that had been reported. A catalysis-extraction circulation process for the synthesis ofl-alanine was established based on high-density fermentation, and the wastewater generated by this process was less than 34% of that by the fermentation process. Our results not only established a new green manufacturing process forl-alanine production fromcis-butenedioic anhydride but also provided a promising strategy that could consider both catalytic ability and cell growth burden for multi-enzyme cascade catalysis.

Fabrication of a stable Ti/Pb-TiOxNWs/PbO2 anode and its application in benzoquinone degradation

Guo, Yingjuan,Tang, Changbin,Xue, Juanqin,Yu, Lihua,Zhang, Lihua

, (2021/01/06)

To delay passivation of a titanium (Ti) substrate as well as enhance adhesion between an electrodeposited PbO2 coating and the Ti substrate, a titanium-lead composite oxide nanowire (Pb-TiOxNWs) intermediate layer was formed in situ on the surface of porous Ti by alkali etching, ion substitution, and high-temperature calcination. At the same time, Ti/PbO2 and Ti/TiO2NWs/PbO2 electrodes with porous Ti as a matrix were prepared for comparison. The surface structure and morphology of the prepared intermediate layer and the PbO2 coating were characterized by scanning electron microscopy (SEM), X-ray diffraction (XRD), and X-ray photoelectron spectroscopy (XPS). The influences of the composite oxide intermediate layer on the electrochemical performance of the PbO2 electrode were analyzed by cyclic voltammetry (CV), linear sweep voltammetry (LSV), and AC impedance spectroscopy (EIS). Accelerated lifetime tests were performed for electrodes with and without different intermediate layers. The results showed that PbOx was incorporated into the titanium dioxide three-dimensional network structure, resulting in formation of Pb-TiOxNWs. The surface of the Ti/Pb-TiOxNWs/PbO2 electrode was denser due to the smaller particle size of PbO2. The preferred crystal orientation of β(110) was observed for PbO2 deposited on Ti/Pb-TiOxNWs. The oxygen evolution potential reached a maximum of 2.19 V for Ti/Pb-TiOxNWs/PbO2. Accelerated life tests showed that compared with Ti/PbO2 and Ti/TiO2NWs/PbO2, the electrode life of Ti/Pb-TiOxNWs/PbO2 was increased by 91.7% and 35.3%, respectively. Therefore, it can be concluded that significantly improved morphology and electrochemical performance were achieved for titanium-based PbO2 electrodes by the addition of a Pb-TiOxNWs intermediate layer. In particular, the electrochemical stability of the PbO2 coating electrodes was improved markedly by the Pb-TiOxNWs intermediate layer. The electrodes were used for electrochemical oxidation of benzoquinone in wastewater (100 mg/L). It was found that chloride ions played a critical role in improving the current efficiency of electro-oxidative degradation. Under the same conditions, the COD removal rate in the presence of NaCl was 45% higher than in the presence of sulfate. The results of HPLC analysis of the intermediate products indicated that the oxidants electro-generated by chloride ions had stronger ring-opening and mineralization capabilities than those electro-generated by sulfate ions.

Process route upstream and downstream products

Process route

(E)-4-(4-nitrophenoxy)-4-oxobut-2-enoic acid

(E)-4-(4-nitrophenoxy)-4-oxobut-2-enoic acid

(2E)-but-2-enedioic acid
110-17-8,26099-09-2

(2E)-but-2-enedioic acid

Conditions
Conditions Yield
With pH=5.1 buffer; polypeptide MN-42; In acetonitrile; at 16.9 ℃; Rate constant; other polypetides vith var. amino acids sequences;
With acetate buffer; JNIIHR polypeptide; In acetonitrile; at 16.85 ℃; pH=5.1; Further Variations:; Reagents; Kinetics;
With AcAPLEPEYPGDNATPEQMHQYAHQLRRYINMLCONH2; In acetate buffer; at 16.85 ℃; pH=4.1; Further Variations:; pH-values; Reagents; Kinetics;
water
7732-18-5

water

thiourea
17356-08-0

thiourea

CYANAMID
420-04-2

CYANAMID

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

hydrogen bromide

(2E)-but-2-enedioic acid
110-17-8,26099-09-2

(2E)-but-2-enedioic acid

Conditions
Conditions Yield
<i>N</i>-[1]naphthyl-aspartic acid diethyl ester

N-[1]naphthyl-aspartic acid diethyl ester

1-amino-naphthalene
134-32-7

1-amino-naphthalene

(2E)-but-2-enedioic acid
110-17-8,26099-09-2

(2E)-but-2-enedioic acid

Conditions
Conditions Yield
4-butanolide
96-48-0

4-butanolide

Butane-1,4-diol
110-63-4

Butane-1,4-diol

4-hydroxybutanoic acid
591-81-1

4-hydroxybutanoic acid

succinic acid
110-15-6

succinic acid

terephthalic acid
100-21-0

terephthalic acid

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

acetic acid

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

propionic acid

(2E)-but-2-enedioic acid
110-17-8,26099-09-2

(2E)-but-2-enedioic acid

Conditions
Conditions Yield
With hydrogen; 0.5percent Pd/0.2percent Re on Rutile TiO2; at 110 ℃; for 170 - 1009h; Product distribution / selectivity;
0.04%
0.28%
4.34%
0%
1.24%
0%
0%
85.51%
0%
0.86%
(R)-4,4,4-trichloro-3-hydroxybutanoic acid
80513-23-1

(R)-4,4,4-trichloro-3-hydroxybutanoic acid

D-Malic acid
636-61-3,78644-42-5

D-Malic acid

(2E)-but-2-enedioic acid
110-17-8,26099-09-2

(2E)-but-2-enedioic acid

Conditions
Conditions Yield
With sodium hydroxide; In water; at 20 ℃; for 24h;
79%
D-Malic acid
636-61-3,78644-42-5

D-Malic acid

(2E)-but-2-enedioic acid
110-17-8,26099-09-2

(2E)-but-2-enedioic acid

Conditions
Conditions Yield
bei der Einw. von Aspergillus niger;
D-Malic acid
636-61-3,78644-42-5

D-Malic acid

(2E)-but-2-enedioic acid
110-17-8,26099-09-2

(2E)-but-2-enedioic acid

Conditions
Conditions Yield
Conditions
Conditions Yield
bei der Einw. von Aspergillus niger;
bromosuccinic acid
923-06-8,584-98-5

bromosuccinic acid

water
7732-18-5

water

D-Malic acid
636-61-3,78644-42-5

D-Malic acid

(2E)-but-2-enedioic acid
110-17-8,26099-09-2

(2E)-but-2-enedioic acid

Conditions
Conditions Yield
l-bromosuccinic acid; Reaktion der Alkali- und Erdalkalisalze der l-Brombernsteinsaeure; und Behandeln der Produkte mit alkal.Medium;
bromosuccinic acid
923-06-8,584-98-5

bromosuccinic acid

silver nitrate

silver nitrate

D-Malic acid
636-61-3,78644-42-5

D-Malic acid

(2E)-but-2-enedioic acid
110-17-8,26099-09-2

(2E)-but-2-enedioic acid

Conditions
Conditions Yield
l-bromosuccinic acid; auch der Reaktion des Natriumsalzes; und Behandeln der Produkte mit alkal. Medium;

Global suppliers and manufacturers

Global( 481) Suppliers
  • Company Name
  • Business Type
  • Contact Tel
  • Emails
  • Main Products
  • Country
  • EAST CHEMSOURCES LIMITED
  • Business Type:Manufacturers
  • Contact Tel:86-532-81906761
  • Emails:josen@eastchem-cn.com
  • Main Products:97
  • Country:China (Mainland)
  • SJZ THLD IMP & EXP CO LTD
  • Business Type:Trading Company
  • Contact Tel:86-311-66699812
  • Emails:kevintangql@263.net
  • Main Products:45
  • Country:China (Mainland)
  • Simagchem Corporation
  • Business Type:Manufacturers
  • Contact Tel:+86-592-2680277
  • Emails:sale@simagchem.com
  • Main Products:110
  • Country:China (Mainland)
  • Hangzhou Dingyan Chem Co., Ltd
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-86465881,86-571-87157530,86-571-88025800
  • Emails:sales@dingyanchem.com
  • Main Products:95
  • 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)
  • COLORCOM LTD.
  • Business Type:Manufacturers
  • Contact Tel:+86-571-89007001
  • Emails:medkem@medkem.cn
  • Main Products:1
  • Country:China (Mainland)
close
Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 110-17-8
Post Buying Request Now
close
Remarks: The blank with*must be completed