Synthesis of methyl furan-2-carboxylate and dimethyl furan-2,5-dicarboxylate by copper-catalyzed reactions of furans with CCl4 and MeOH

Хуснутдинов, Р. И.; Bayguzina, А. R.; Mukminov, R. R.

doi:10.1007/s11172-013-0012-6

Cited by 9 publications

(6 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…MS (GC–MS, 70 eV): m / z (%)=200 (5) [ M + ], 169 (100), 153 (4), 141 (10), 123 (20), 109 (3), 95 (3), 82 (3), 75 (10), 67 (3), 59 (7), 53 (4), 39 (8). Values correspond to those previously reported by Khusnutdinov et al …”

Section: Methodssupporting

confidence: 92%

“…1 H NMR (400.17 MHz, [D 6 ]DMSO): δ =9.75 (1 H, s), 7.62 (1 H, d, J= 3.8 Hz), 7.49 (1 H, d, J= 3.8 Hz), 3.88 ppm (3 H, s); MS (GC–MS, 70 eV): m / z (%)=154 (55) [ M + ], 123 (100), 109 (2), 95 (24), 67 (6), 53 (5), 39 (23). NMR (CDCl 3 ) spectroscopy and MS corresponded to the values reported by Khusnutdinov et al . and the NMR in [D 6 ]DMSO corresponded to the values reported by Shackelford et al .…”

Section: Methodssupporting

confidence: 85%

See 1 more Smart Citation

Synthesis of Furandicarboxylic Acid Esters From Nonfood Feedstocks Without Concomitant Levulinic Acid Formation

Klis

Haveren

et al. 2017

ChemSusChem

View full text Add to dashboard Cite

Abstract5‐Hydroxymethylfurfural (HMF) is a versatile intermediate in biomass conversion pathways. However, the notoriously unstable nature of HMF imposes challenges to design selective routes to chemicals such as furan‐2,5‐dicarboxylic acid (FDCA). Here, a new strategy for obtaining furans is presented, bypassing the formation of the unstable HMF. Instead of starting with glucose/fructose and thus forming HMF as an intermediate, the new route starts from uronic acids, which are abundantly present in many agro residues such as sugar beet pulp, potato pulp, and citrus peels. Conversion of uronic acids, via ketoaldonic acids, to the intermediate formylfuroic acid (FFA) esters, and subsequently to FDCA esters, proceeds without formation of levulinic acid or insoluble humins. This new route provides an attractive strategy to valorize agricultural waste streams and a route to furanic building blocks without the co‐production of levulinic acid or humins.

show abstract

Section: Methodssupporting

confidence: 92%

Section: Methodssupporting

confidence: 85%

Synthesis of Furandicarboxylic Acid Esters From Nonfood Feedstocks Without Concomitant Levulinic Acid Formation

Klis

Haveren

et al. 2017

ChemSusChem

View full text Add to dashboard Cite

show abstract

“…To reduce the operation cost and enhance commercial interest, the solution after the reaction and the FDCA dissolved in the reaction solution need to be further recycled. To meet the standards of the polyester industry, the crude FDCA prepared by oxidation needs to be further purified by crystallization in binary acetic acid + water solvent mixtures or by esterification with methanol or ethanol to give dimethyl furan-2,5-dicarboxylate or diethyl furan-2,5-dicarboxylate, respectively, with the formation of water. − Thus, the solubilities of FDCA in binary acetic acid + water, methanol + water, and ethanol + water solvent mixtures are required in order to determine the feed composition, reaction and crystallization conditions, etc., and the solubilities of FDCA in these binary solvent mixtures are essential solid–liquid equilibrium data for these processes. Unfortunately, there are no literature reports about the solubilities of FDCA in these solvent mixtures.…”

Section: Introductionmentioning

confidence: 99%

Solubilities of 2,5-Furandicarboxylic Acid in Binary Acetic Acid + Water, Methanol + Water, and Ethanol + Water Solvent Mixtures

et al. 2018

View full text Add to dashboard Cite

The solubilities of 2,5-furandicarboxylic acid (FDCA) in binary acetic acid + water, methanol + water, and ethanol + water solvent mixtures were measured by a static analytical method with the mass fraction of water in the solvent varying from 0 to 0.3 at atmospheric pressure. Furthermore, the molar enthalpy of fusion (Δ fus H = 55.131 kJ/mol) and fusion temperature (T fus = 614.45 K) of FDCA were determined by differential scanning calorimetry. The non-random two liquid (NRTL) model and the measured parameters were used to correlate these solubility data, and the relevant parameters were regressed by the least-squares method. The NRTL model was found to provide a satisfactory representation of the experimental data.

show abstract

“…The direct carboxylation of furoic acid or methylation followed by carboxylation of furan derivatives was also reported. Khusnutdinov et al . studied the direct synthesis of dimethyl furan 2,5‐dicarboxylate with Cu salts and CCl 4 .…”

Section: Homogeneous Catalysismentioning

confidence: 99%

Recent Advances in Carboxylation of Furoic Acid into 2,5‐Furandicarboxylic Acid: Pathways towards Bio‐Based Polymers

et al. 2020

View full text Add to dashboard Cite

2,5-furandicarboxylic acid (FDCA) is one of the most important bio-sourced building blocks and several routes have been reported for its synthesis. FDCA is presumed to be an ideal green alternative to terephthalate, which is one of the predominant monomers in polymer industry. This Minireview concerns the synthesis of FDCA by using various carboxylation reactions and discusses the synthesis of FDCA starting from furoic acid and CO 2 and using different catalytic and stoichiometric processes. This process is of high interest, as it avoids the glucose isomerization step and selectivity issues observed during the 5-hydroxymethylfurfural oxidation step of the current alternative route to FDCA. Discussion focuses on the main parameters that govern selectivity and activity in the carboxylation processes. Moreover, various previously described processes, such as the Henkel reaction and enzymatic, homogeneous catalytic, and photoelectrocatalytic processes, are also discussed.

show abstract

Synthesis of methyl furan-2-carboxylate and dimethyl furan-2,5-dicarboxylate by copper-catalyzed reactions of furans with CCl4 and MeOH

Cited by 9 publications

References 17 publications

Synthesis of Furandicarboxylic Acid Esters From Nonfood Feedstocks Without Concomitant Levulinic Acid Formation

Synthesis of Furandicarboxylic Acid Esters From Nonfood Feedstocks Without Concomitant Levulinic Acid Formation

Solubilities of 2,5-Furandicarboxylic Acid in Binary Acetic Acid + Water, Methanol + Water, and Ethanol + Water Solvent Mixtures

Recent Advances in Carboxylation of Furoic Acid into 2,5‐Furandicarboxylic Acid: Pathways towards Bio‐Based Polymers

Contact Info

Product

Resources

About