A Convenient, High-Yield Preparation of Butadiene-2,3-Dicarboxylic Acid (Fulgenic Acid)

Recently, we have developed an eco-friendly method for the preparation of a renewable dicarboxylic acid 2,5-furandicarboxylic acid (FDCA) from biomass-based 5-hydroxymethylfrufural (HMF). In the present work, we optimized our reported method, which used phosphate buffer and Fe(OH)3 as the stabilizer to improve the stability of potassium ferrate, then got a purified FDCA (up to 99%) in high yield (91.7 wt %) under mild conditions (25 °C, 15 min, air atmosphere). Subsequently, the obtained FDCA, along with 1,6-hexanediol (HDO), which was also made from HMF, were used as monomers for the synthesis of poly(hexylene 2,5-furandicarboxylate) (PHF) via direct esterification, and triphenyl phosphite was used as the antioxidant to alleviate the discoloration problem during the esterification. The intrinsic viscosity, mechanical properties, molecular structure, thermal properties, and degradability of the PHFs were measured or characterized by Koehler viscometer, universal tensile tester, Nuclear Magnetic Resonance (NMR), Fourier-transform Infrared (FTIR), X-ray diffraction (XRD), Differential Scanning Calorimeter (DSC), Derivative Thermogravimetry (DTG), Scanning Electron Microscope (SEM), and weight loss method. The experimental evidence clearly showed that the furan-aromatic polyesters prepared from biomass-based HMF are viable alternatives to the petrochemical benzene-aromatic polyesters, they can serve as low-melting heat bondable fiber, high gas-barrier packaging material, as well as specialty material for engineering applications.

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The Baeyer-Villiger oxidation of a-substituted cyclic ketones

Australian Journal of Chemistry ◽

10.1071/ch9640440 ◽

1964 ◽

Vol 17 (4) ◽

pp. 440 ◽

Cited By ~ 5

Author(s):

JE Bolliger ◽

JL Courtney

Keyword(s):

Dicarboxylic Acid ◽

Carbonyl Group ◽

Steric Hindrance ◽

Peracetic Acid ◽

High Yield ◽

Acid Oxidation ◽

Cyclic Ketones ◽

Villiger Oxidation

The Baeyer-Villiger oxidation of 2-chlorocholestan-3-one and 2-bromo-cholestan-3-one gives the corresponding α-halo-lactones (VIIIa) and (VIIIc). The α-bromo-lactone is readily rearranged and converted into 2-methoxycarbonyl-3-oxa-5α-cholestane (Va) by boiling methanol but the α-choloro-lactone is unaffected by this treatment. Both the a-bromo-lactone and the or-chloro-lactone react with alkali to form 2-carboxy-3-oxa-5α-cholestane (Vb). α-Iodocholestan-3-one is unexpectedly converted into cholest-1-en-3-one in about 50% yield by trifluoro-peracetic acid. �� 2-Bromofriedelan-3-one did not undergo a Baeyer-Villiger reaction under the usual conditions, probably owing to the steric hindrance of the carbonyl group. The per-acid oxidation of 2β-hydroxyfriedelan-3-0110 yielded mainly the 2,3-seco-dicarboxylic acid and a smaller amount of the expected α-hydroxy-lactone. However 2β-acetoxyfriedelan-3-one underwent a Baeyer-Villiger oxidation in the expected fashion to give a high yield of the 2-acetoxy-lactone.

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Novel and Efficient Procedure for the Preparation of Two Pyridine Dicarboxylic Acid Derivatives

E-Journal of Chemistry ◽

10.1155/2011/120730 ◽

2011 ◽

Vol 8 (1) ◽

pp. 449-452 ◽

Cited By ~ 2

Author(s):

G. U. Guoliang ◽

L. U. Ming

Keyword(s):

Green Chemistry ◽

Dicarboxylic Acid ◽

High Purity ◽

High Yield ◽

Efficient Procedure ◽

Pyridine Dicarboxylic Acid ◽

Vinyl Pyridine ◽

Synthesis Procedure ◽

New Strategies

New strategies for the synthesis of two pyridine dicarboxylic acid derivatives namely; 4-(2-(2,6-dicarboxypyridin-4-yl)vinyl)pyridine-2,6-dicarboxylic acid and 2,6-bis(2-(2,6–dicarboxy-pyridin-4-yl)vinyl)pyridine have been described. New oxidant used is a good example of green chemistry technology and the synthesis procedure harvest a high-purity product at a high yield.

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Synthesis of norbornene derivatives and their polymers via ROMP of norbornene derivatives

High Performance Polymers ◽

10.1177/0954008319900536 ◽

2020 ◽

Vol 32 (6) ◽

pp. 729-737

Author(s):

Haoyang Yu ◽

Shaohui Lin ◽

Daniel Sun ◽

Qinmin Pan

Keyword(s):

Dicarboxylic Acid ◽

Ring Opening ◽

Dimethyl Ester ◽

Polymerization Process ◽

High Yield ◽

Broad Application ◽

Metathesis Polymerization ◽

Molecular Weights ◽

Norbornene Derivatives ◽

Application Prospects

Dicyclopentadiene (DCPD) is a by-product resulting from the ethylene industry, which is high yield and underused in China. A technical route of producing valuable products—norbornene derivatives and their polymers from DCPD—was proposed and studied in this research. 5-Norbornene-2,3-dicarboxylic anhydride, a downstream product of DCPD, was employed as starting material to synthesize norbornene derivatives. Norbornene derivatives, 5-norbornene-2,3-dicarboxylic acid dimethyl ester and 5-norbornene-2,3-dicarboxylic acid diphenylethyl esters, as well as their polymers have broad application prospects in many areas. Ring-opening metathesis polymerization was employed as the polymerization process, and the polymers/copolymers of norbornene derivatives were obtained successfully. The polymerization process of norbornene derivatives was investigated in detail, from which the method for controlling molecular weights and decomposition temperatures of norbornene derivatives copolymers were developed. Till now, the route of generating valuable norbornene derivatives from DCPD was completed finally.

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ChemInform Abstract: A CONVENIENT, HIGH-YIELD PREPARATION OF BUTADIENE-2,3-DICARBOXYLIC ACID (FULGENIC ACID)

Chemischer Informationsdienst ◽

10.1002/chin.197449186 ◽

1974 ◽

Vol 5 (49) ◽

pp. no-no

Author(s):

P. DOWD ◽

K. KANG

Keyword(s):

Dicarboxylic Acid ◽

High Yield

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ChemInform Abstract: A High-Yield Route to 1,2-Dihydrocyclobutabenzene-3,6-dicarboxylic Acid.

ChemInform ◽

10.1002/chin.199323171 ◽

2010 ◽

Vol 24 (23) ◽

pp. no-no

Author(s):

K. A. WALKER ◽

L. J. MARKOSKI ◽

J. S. MOORE

Keyword(s):

Dicarboxylic Acid ◽

High Yield

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Quality films from carbon fiber evaporation for thorough coverage of TEM grids

Proceedings, annual meeting, Electron Microscopy Society of America ◽

10.1017/s0424820100104157 ◽

1988 ◽

Vol 46 ◽

pp. 418-419

Author(s):

N. Tempel ◽

M. C. Ledbetter

Keyword(s):

Electron Microscopy ◽

High Resolution Electron Microscopy ◽

Carbon Films ◽

Low Noise ◽

Vacuum Evaporation ◽

High Yield ◽

Good Adhesion ◽

Noise Structure ◽

Resolution Electron ◽

Carbon Foils

Carbon films have been a support of choice for high resolution electron microscopy since the introduction of vacuum evaporation of carbon. The desirable qualities of carbon films and methods of producing them has been extensively reviewed. It is difficult to get a high yield of grids by many of these methods, especially if virtually all of the windows must be covered with a tightly bonded, quality film of predictable thickness. We report here a method for producing carbon foils designed to maximize these attributes: 1) coverage of virtually all grid windows, 2) freedom from holes, wrinkles or folds, 3) good adhesion between film and grid, 4) uniformity of film and low noise structure, 5) predictability of film thickness, and 6) reproducibility.Our method utilizes vacuum evaporation of carbon from a fiber onto celloidin film and grid bars, adhesion of the film complex to the grid by carbon-carbon contact, and removal of the celloidin by acetone dissolution. Materials must be of high purity, and cleanliness must be rigorously maintained.

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Effects of high pressure on the crystallization of carbon fiber reinforced polyetheretherketone (CF/PEEK) laminate composites

Proceedings, annual meeting, Electron Microscopy Society of America ◽

10.1017/s0424820100177519 ◽

1990 ◽

Vol 48 (4) ◽

pp. 876-877

Author(s):

Hong-Ming Lin ◽

C. H. Liu ◽

R. F. Lee

Keyword(s):

High Pressure ◽

Carbon Fiber ◽

Sample Surface ◽

High Yield ◽

Fiber Reinforced ◽

Laminate Composites ◽

Peek Composite ◽

Continuous Carbon Fiber ◽

Carbon Fiber Reinforced

Polyetheretherketone (PEEK) is a crystallizable thermoplastic used as composite matrix materials in application which requires high yield stress, high toughness, long term high temperature service, and resistance to solvent and radiation. There have been several reports on the crystallization behavior of neat PEEK and of CF/PEEK composite. Other reports discussed the effects of crystallization on the mechanical properties of PEEK and CF/PEEK composites. However, these reports were all concerned with the crystallization or melting processes at or close to atmospheric pressure. Thus, the effects of high pressure on the crystallization of CF/PEEK will be examined in this study.The continuous carbon fiber reinforced PEEK (CF/PEEK) laminate composite with 68 wt.% of fibers was obtained from Imperial Chemical Industry (ICI). For the high pressure experiments, HIP was used to keep these samples under 1000, 1500 or 2000 atm. Then the samples were slowly cooled from 420 °C to 60 °C in the cooling rate about 1 - 2 degree per minute to induce high pressure crystallization. After the high pressure treatment, the samples were scanned in regular DSC to study the crystallinity and the melting temperature. Following the regular polishing, etching, and gold coating of the sample surface, the scanning electron microscope (SEM) was used to image the microstructure of the crystals. Also the samples about 25mmx5mmx3mm were prepared for the 3-point bending tests.

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