A scalable carboxylation route to furan-2,5-dicarboxylic acid

2017 ◽  
Vol 19 (13) ◽  
pp. 2966-2972 ◽  
Author(s):  
Graham R. Dick ◽  
Amy D. Frankhouser ◽  
Aanindeeta Banerjee ◽  
Matthew W. Kanan
Keyword(s):  
Dicarboxylic Acid ◽  
High Yield ◽  
Furoic Acid

2-Furoic acid is converted to furan-2,5-dicarboxylic acid in high yield on a mole scale using carbonate-promoted C–H carboxylation.

A High-Yield Route to 1,2-Dihydrocyclobutabenzene-3,6-dicarboxylic Acid

Synthesis ◽  
1992 ◽  
Vol 1992 (12) ◽  
pp. 1265-1268 ◽  
Author(s):  
Kenneth A. Walker ◽  
Larry J. Markoski ◽  
Jeffrey S. Moore
Keyword(s):  
Dicarboxylic Acid ◽  
High Yield

scholarly journals An Eco-Friendly Method to Get a Bio-Based Dicarboxylic Acid Monomer 2,5-Furandicarboxylic Acid and Its Application in the Synthesis of Poly(hexylene 2,5-furandicarboxylate) (PHF)

Polymers ◽  
2019 ◽  
Vol 11 (2) ◽  
pp. 197 ◽  
Author(s):  
Junhua Zhang ◽  
Qidi Liang ◽  
Wenxing Xie ◽  
Lincai Peng ◽  
Liang He ◽  
...  
Keyword(s):  
Dicarboxylic Acid ◽  
High Yield ◽  
Potassium Ferrate ◽  
Air Atmosphere ◽  
Tensile Tester ◽  
Weight Loss Method ◽  
Furandicarboxylic Acid ◽  
Loss Method ◽  
The Stability ◽  
Aromatic Polyesters

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.

The Baeyer-Villiger oxidation of a-substituted cyclic ketones

1964 ◽  
Vol 17 (4) ◽  
pp. 440 ◽  
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.

A sustainable and green route to furan-2,5-dicarboxylic acid by direct carboxylation of 2-furoic acid and CO2

2021 ◽  
Vol 48 ◽  
pp. 101524
Author(s):  
Yu-Gao Wang ◽  
Chong-Yang Guo ◽  
Jun Shen ◽  
Yu-Qin Sun ◽  
Yan-Xia Niu ◽  
...  
Keyword(s):  
Dicarboxylic Acid ◽  
Furoic Acid ◽  
Green Route

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

2011 ◽  
Vol 8 (1) ◽  
pp. 449-452 ◽  
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.

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

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.

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

ChemInform ◽  
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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