* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
General procedure: Esterification of levulinic acid was carried out in a 50mL round bottom flask equipped with a reflux condenser. In a typical catalytic reaction the catalyst (40mg) was added to a mixture of levulinic acid and ethanol with the molar ratio of LA: alcohol=1:8 (ethanol acts as reagent cum solvent) and the mixture was magnetically stirred at 333K for 2h. A portion of the reaction mixture was separated after the scheduled reaction time through filtration and the filtrate was then analyzed through the gas chromatography (GC) equipped with a flame-ionized detector and a capillary column. All compounds were characterized on the basis of their spectroscopic data (1H NMR) and by comparison with those reported in the literature.
Reference：
[1] RSC Advances, 2016, vol. 6, # 3, p. 2106 - 2111
[2] Journal of the American Chemical Society, 1930, vol. 52, p. 4883
[3] Journal of the American Chemical Society, 1933, vol. 55, p. 3393
[4] Patent: US2029412, 1934, ,
[5] Journal fuer Praktische Chemie (Leipzig), 1955, vol. <4> 1, p. 153,154
[6] Patent: WO2010/102203, 2010, A2, . Location in patent: Page/Page column 26-27
[7] Green Chemistry, 2014, vol. 16, # 2, p. 785 - 791
[8] Journal of Molecular Catalysis A: Chemical, 2017, vol. 426, p. 30 - 38
[9] Applied Catalysis A: General, 2017, vol. 547, p. 237 - 247
[10] Catalysis Today, 2018, vol. 309, p. 253 - 262
Reference：
[1] Green Chemistry, 2014, vol. 16, # 3, p. 1436 - 1443
[2] ChemCatChem, 2014, vol. 6, # 11, p. 3080 - 3083
[3] Russian Journal of Applied Chemistry, 2007, vol. 80, # 10, p. 1687 - 1690
[4] ChemSusChem, 2011, vol. 4, # 1, p. 112 - 118
[5] RSC Advances, 2016, vol. 6, # 93, p. 90232 - 90238
[6] Patent: WO2010/102203, 2010, A2, . Location in patent: Page/Page column 26-27
[7] Catalysis Letters, 2018, vol. 148, # 6, p. 1731 - 1738
[8] Patent: US2763665, 1952, ,
[9] Catalysis Communications, 2019, p. 62 - 66
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[ 6347-01-9 ]
[ 645-67-0 ]
Reference：
[1] Green Chemistry, 2014, vol. 16, # 2, p. 785 - 791
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[ 71-23-8 ]
[ 57-50-1 ]
[ 1917-66-4 ]
[ 645-67-0 ]
Yield
Reaction Conditions
Operation in experiment
65 %Spectr.
at 180℃; for 40 h;
1.8 g of sucrose,0.361 g of SnCl4, 0. 058 g of BF3?, 20? Of n-propanol were added to 50 mLStainless steel-lined reactor with Teflon,Heated to 180 ° C,The reaction was carried out at that temperature for 40 h. Filtration,To remove unreacted sucrose and other insoluble impurities,The solvent was removed by rotary evaporation,2 mL H20 was added and the organic phase was extracted with methyl isobutyl ketone,The resulting organic phase was rotary evaporated to a high purity furan derivative,The isolated yield was 89percent. The qualitative analysis of the reaction products was carried out by gas chromatography-mass spectrometry (GC-MS)And with the standard material (HMF,Propoxyl methyl furfural and propyl propionate)The retention times in gas chromatography (GC) were compared and confirmed. Quantitative analysis of the yield distribution of different furan derivatives was determined by 4 NMR,The product distribution results are:5-propoxymethylfurfural was 65percent,HMF was 0percent and propyl levulinate was 35percent.
1.8 g of sucrose,0.271 g of GeCl4, 0.091 g of BBr3, and 20 mL of n-propanol were added to 50 mL of a polyTetrafluoroethylene-lined stainless steel reactor,Heated to l00 ° C,The reaction was carried out at that temperature for 10 h. Filtration,To remove unreacted sucrose and other insoluble impurities,The solvent was removed by rotary evaporation,2 mL H20 was added and the organic phase was extracted with methyl isobutyl ketone,The resulting organic phase was rotary evaporated to a high purity furan derivative,The isolated yield was 83percent. The qualitative analysis of the reaction products was carried out by gas chromatography-mass spectrometry (GC-MS)And with the standard material (HMF,5-propoxymethylfurfural and propyl propionate) in gas chromatography (GC) were compared and confirmed. Quantitative analysis of the yield distribution of different furan derivatives was confirmed by 1H NMR,The product distribution results are:5-propoxymethylfurfural was 72percent, HMF was 9percentPropyl propionate was 19percent
After mixing 50 grams of furfuryl alcohol, 375 grams of propanol, 10 grams of water, and 20 grams of SO42- / MxOy super strong acid, the reaction is carried out at a temperature of 80 C, and the stirring speed is controlled to 600 rpm, the condensation reflux temperature is 20 C, the reaction After 5 hours, after the temperature was lowered to room temperature, the catalyst was removed by filtration, and the propanol in the reaction mixture was distilled off under reduced pressure at 45 C to obtain light yellow propyl levulinate, which was analyzed by high performance liquid chromatography, the conversion rate of furfuryl alcohol and acetyl The yields of propyl propionate were 100% and 97.76%, respectively, and the yield was 97.76%.
sulfuric acid; In n-propyl levulinate; water; at 120℃; for 2.95h;
Example 7; A 2 L two-neck flask equipped with a magnetic stir bar, a Dean-Stark trap, and a thermocouple was charged with 232.52g (2.002mol) levulinic acid (obtained from the Langfang Triple Well Chemicals Company, Ltd. of Langfang City, HeBei, China), 241.52g (4.019 mol) n-propanol (>;99.8%, obtained from the Sigma-Aldrich Company of St. Louis, MO), 600 mL toluene, and 2 mL cone, sulfuric acid. The reaction was heated on a heating mantle to reflux. After refluxing overnight, total amount of 42.7 mL of water was collected and removed from the Dean-Stark trap. The reaction flask was allowed to cool to room temperature. Then 100 g basic alumina (obtained from the Sigma-Aldrich Company of St. Louis, MO) was added to the reaction solution and stirred for about 80 minutes. The solids were then filtered off, and the filtrate was concentrated on a rotary evaporator with the filtrate in a flask immersed in an oil bath set to 750C and 15 Torr vacuum to remove toluene and n- propanol. The residue was distilled on the rotary evaporator in a flask immersed in an oil bath set to 110-120C and 15 Torr vacuum to yield 284.48 g colorless liquid in the catch flask. The product was determined by GC-MS to be 99.51% n-propyl levulinate.The procedure of Example 1 was used to generate a profile of boiling points using n-propanol and n-propyl levulinate. The measured boiling points are shown in Table 3.Table 3. Boiling points of n-propanol/n-propyl levulinate mixtures. A 500 niL four-neck flask was equipped with a magnetic stir bar, a dropping funnel, a condenser, and a thermocouple. The flask was charged with 100.02g (0.632mol) n-propyl levulinate (synthesized from levulinic acid as described above), 16.48g (0.274mol) n-propanol, 1.463 mL deionized water, and 0.575 mL cone, sulfuric acid. The mixture was heated with a heating mantle to a temperature at 1200C. A mixture of 49.07g (0.495mol) furfuryl alcohol (99%, obtained from Acros Organics of Geel, Belgium) and 43.06g (0.716 mol) n-propanol was added to the reaction mixture dropwise over about 117 minutes. The reaction was refluxed for additional 1 hour after addition was complete. Then the reaction flask was allowed to cool to room temperature. The crude reaction mixture appeared to be homogeneous, with no insoluble or phase-separated material observed. About 50.1O g of the reaction mixture was transferred to a 250 mL flask and distilled using a Kugelrohr apparatus at about 4-8 Torr and an air bath temperature of up to about 1790C.After distillation, total amount of undistillable solid left in the flask was 1.16 g, which contained 0.25 g sulfuric acid and 0.91 g of a tarry residue. Ratio of the amount of tarry residue formed in the reaction to the amount of furfuryl alcohol added was 7.8%. GC-MS analysis of the crude reaction product was carried out as for Example 2 and showed that n-propyl levulinate was present at 99.1%.
With silica-alumina; at 180℃;
General procedure: The catalytic activity experiments were conducted in a fixed bed quartz reactor (14 mm id and 280 mm length)at atmospheric pressure. In each catalytic experiment, 250 mg of catalyst is diluted with equal amount of quartz particles and placed at the centre of the reactor. Priorto the reaction, the catalyst was flushed in a N2 flow of1800 mL h-1 at 180 C for 1 h. The liquid feed withrequired molar ratio of FAL to alcohol was continuouslyfed at a liquid hour space velocity (LHSV) of 1 h-1 usinga feed pump (M/s. B. Braun Co., Germany). Unless otherwisespecified the reaction conditions are same. The liquidproduct mixture was collected in an ice cold trap andanalyzed at regular intervals. This product mixture wasanalyzed by a flame ionization detector (FID) equippedgas chromatograph, GC-17A (M/s. Shimadzu Instruments,Japan) with EB-5 capillary column (30 m × 0.53 mm ×5.0 μm) and the product components were confirmed byusing GC-MS, QP-2010 (M/s. Shimadzu Instruments, Japan) with EB-5 MS capillary column (30 m × 0.25 mm× 0.25 μm).
With zeolite HZSM-5 (SAR95) catalyst; for 6h;Reflux;
In a typical procedure, the alcoholysis of furfuryl alcohol was performedin a liquid phase batch reaction under magnetic stirring at thedesired temperature. The required molar composition of furfuryl alcoholand butanol, and the catalyst (with respect to the total reactants) weretaken in a 25 mL round bottom flask connected to a condenser. Thereaction of furfuryl alcohol was also conducted with other alcohols witha similar procedure under reflux conditions. The samples of the reactionmixture were periodically collected and quantitatively analyzed by gaschromatography (GC) (Agilent Technologies 7820A) equipped with HP-5 capillary column (0.25 mm I.D., 30 m length) coupled with the flameionization detector. The identity of the products was confirmed by Gaschromatography mass spectrometry (GCMS). The furfuryl alcohol conversionand butyl levulinate selectivity were determined using theexternal standard method in the GC.
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