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

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

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

Polymers ◽  
2019 ◽  
Vol 11 (2) ◽  
pp. 197 ◽  
Author(s):  
Junhua Zhang ◽  
Qidi Liang ◽  
Wenxing Xie ◽  
Lincai Peng ◽  
Liang He ◽  
...  

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.


1964 ◽  
Vol 17 (4) ◽  
pp. 440 ◽  
Author(s):  
JE Bolliger ◽  
JL Courtney

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.


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

2011 ◽  
Vol 8 (1) ◽  
pp. 449-452 ◽  
Author(s):  
G. U. Guoliang ◽  
L. U. Ming

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.


2020 ◽  
Vol 32 (6) ◽  
pp. 729-737
Author(s):  
Haoyang Yu ◽  
Shaohui Lin ◽  
Daniel Sun ◽  
Qinmin Pan

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 ◽  
2010 ◽  
Vol 24 (23) ◽  
pp. no-no
Author(s):  
K. A. WALKER ◽  
L. J. MARKOSKI ◽  
J. S. MOORE
Keyword(s):  

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