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Like in Example 9, a 12 ml., stainless steel reactor was charged with 0.S g of FDCA, 5 mL of ethanol, and an excess of dry ice crystals. The reactor is closed and heated to 2 \ 0°C for 5 hours in a sand bath. The internal reaction pressure was between about 1 00 psig and 2200 psig. After 5 hours the reactor is cooled. The contents were dried and analyzed as above. The reaction mixture contained diethyl ester ( -82.1 percent), monoethyi ester (-15.6percent}, and unrcacted FDCA (-2.4percent).
51.6%
at 180℃; for 4 h; Autoclave; Green chemistry
Charging a 1 liter (L) autoclave reactor with 5 g. of 2,5-furan dicarhoxylic acid and 300 mL ofethano, the reactor was pressurized initially with 400 psig of C(. The reaction mixture was heated to about 180°C and maintained at this temperature for 4 hours. During this timer the pressure inside the reactor increase from 400 psig to about 1600 psig. After 4 hours at. 180°C, the reactor was cooled to ambient room temperature and depressurized. The contents of the reactor were filtered, dried overnight under vacuum, and analyzed tor conversion using GC/MS. The reaction mixture contained diethyl ester t -22.7 wt.percent), monoethyl ester (-51 .6 wt.percent) and unreacted FDCA ( -25.8 wt.percent).
With sulfuric acid In water at 78℃; for 67 h; Dean-Stark
2,5-furandicarboxylic acid (25.18 g; 160 mmol) was added to ethanol (1,800 mL).Aqueous sulfuric acid (1.32 mL) was added. The mixture was heated at reflux (about78°C) for 67 hours, during which time water was removed from the reaction by the use ofa Dean-Stark apparatus. The reaction progress was monitored using NMR spectroscopy. After the 2,5-diethyl-2,5-furandicarboxylate had been formed in >97percent purity by NMR, the reaction mixture was allowed to cool to ambient temperature and was extracted with 2- methyltetrahydrofuran. The combined organic layers were washed with a saturated aqueous brine solution and deionised water, and dried (Mg504). The organics werefiltered and the volatiles were removed in vacuo to afford the title compound (26.77 g; 130 mmol; >98percent conversion).
98%
for 18 h; Reflux; Inert atmosphere
To a solution of 2,5-furandicarboxylic acid (1.00 g, 6.41 mmol) in dry EtOH (50 mL) was added aqueous 98percent sulfuric acid(0.05 mL) and the resulting solution heated at reflux for 18 h under a nitrogen atmosphere. The solution was cooled and concentrated in vacuo. The resulting residue was filtered and washed with saturated aqueous NaHCO3 solution (3x 10 mL) and water (3x 10 mL) to afford diethyl furan-2,5-dicarboxylate as a white solid (1.33 g, 98percent). Experimental data as per literature. ADDIN EN.CITE Sigeru19711944194194017Torii SigeruTanaka HideoOgo Hitosi Yamasita Siro Anodic Reaction of 5-Alkyl-2-furoic Acids in Protic Solvents Bulletin of the Chemical Society of JapanBulletin of the Chemical Society of JapanBull. Chem. Soc. Jpn.1079-108444197141H NMR (500 MHz, CDCl3) δ1.38 (t, J = 7.1 Hz, 6H), 4.39 (q, J = 7.1 Hz, 4H), 7.19 (s, 2H). 13C NMR (125 MHz, CDCl3) δ 14.2, 61.6, 118.2, 146.9, 158.1.
97%
at 220℃; for 4 h;
A stirred tank reactor (total volume 100 mL) was charged with 30 mL 1- butanol, FDCA. and Siralox 30/350 in powder form (silica-alumina, Al2O3:SiO2=70 :30, Sasol Germany GmbH). The reactor was purged with nitrogen and heated to 220°C giving an autogenous reactor pressure of up to 15 bar. The reaction time measurement started upon switching-on the reactor heating. While running the experiment, the agitation speed was kept constant at 800 rpm.After t-240 min, the reactor was cooled down, the catalyst was filtrated and the reaction solution was analyzed by high-performance liquid chromatography (HPLC) . The initial amount of FDCA and the catalyst amount were varied as shown in table 5.Example 6FDCA was esterified in the same manner as shown in example 5, except that ethanol was used instead of 1-butanol.
Reference：
[1] Patent: WO2016/202858, 2016, A1, . Location in patent: Page/Page column 57
[2] Bioorganic and Medicinal Chemistry Letters, 2018,
[3] Patent: WO2012/101015, 2012, A1, . Location in patent: Page/Page column 19-20
[4] Polish Journal of Chemistry, 2001, vol. 75, # 12, p. 1943 - 1946
[5] Organic and Biomolecular Chemistry, 2014, vol. 12, # 46, p. 9324 - 9328
[6] Justus Liebigs Annalen der Chemie, 1878, vol. 193, p. 187
[7] Chemische Berichte, 1901, vol. 34, p. 3447
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