* 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.
Stage #1: at 80℃; for 3 h; Inert atmosphere Stage #2: at 130℃;
Step 1, Preparation of choline-based acidic ionic liquid: 0.5mol choline chloride was heated under agitation flask was added 500mL, 0.25mol of citric acid was added, under a nitrogen atmosphere, the conditions of temperature 80 3h, after cooling to give choline-based acidic ionic liquid;Step 2, the esterification reaction: to a stirred with a mechanical, a thermometer, a reflux condenser and a four-necked flask was added 1.0mol trap n-butanol and a step in the choline-based acidic ionic liquid was heated to reflux with stirring the reaction water was separated from the trap, the reaction of the reaction to dryness stopped when re-entering the trap, choline chloride precipitates from the reaction system; the stirring was heated at reflux temperature of 130 , the stirring rate to 1000rpm;Step 3, separated choline chloride: The reaction system of Step II reaction was filtered to obtain a solid product and a liquid phase of choline chloride;Step 4, tributyl citrate purification: step 3 of the liquid product was subjected to atmospheric distillation, and then using mass concentration of 8percent NaHCO3Mass concentration of the solution or NaOH solution (also can be mass concentration of 1percent to 3percent of 1percent to 5percent Na2CO3Alternatively the solution pH) after the residue was washed atmospheric distillation residue to a value of 6, followed by activated carbon was added to the residue decolorized after washing, the activated carbon was removed by filtration, and then the residue was distilled under reduced pressure after filtration, the pressure is 260 Pa, the fraction collected 197 ~ 200 obtain tributyl citrate; the atmospheric distillation temperature of 119 deg.] C; mass of the activated carbon was 5.0percent by mass of citric acid in step a.
94.1%
at 95 - 143℃; for 6.33333 h;
A 1 L four-necked flask equipped with a stirrer, thermometer, condenser and distillate receiver was charged with 192.0 g (1.0 mole) of anhydrous citric acid, 267.0 g (3.6 moles) of butanol and 1.9 g of sulfuric acid. The mixture was heated to 95°C over a period of 20 minutes while being stirred at atmospheric pressure. While recovering butanol and water generated as by-products of esterification in the receiver, stirring was continued for 3 hours until the reaction temperature reached 105°C. Subsequently, while recovering butanol and water generated as by-products of esterification in the receiver, 222.0 g (3.0 moles) of additional butanol was added at a reaction temperature of 101 to 143°C over a period of 3 hours to complete the reaction. After the completion of the reaction, the reaction product was cooled to 60°C, and at the same temperature (60°C), neutralized by adding sodium carbonate in an amount corresponding to twice the acid value of the reaction product (i.e., 2.0 g) and 120.0 g of water. Subsequently, the organic layer was washed with 120.0 g of water and heated to 120°C. Excess butanol was recovered until the pressure reached about 4 kPa, and steam distillation was performed at the same pressure at 120°C for 1 hour to remove low-boiling components from the reaction product, to thereby obtain 329.0 g of a colorless transparent liquid. The yield was 94.1percent and the acid value of the product was 0.025 (mg KOH/g).
84.4%
With toluene-4-sulfonic acid In toluene at 90 - 110℃; for 4 h;
With a stirrer,Trap,Snake-shaped condenser,Necked flask equipped with a stirrer and a thermometer, 3.6 mol (266.4 g) of n-butanol was added,Citric acid 0.6 mol (210 g),P-toluenesulfonic acid (9.53 g)Toluene 50 ml.During heating from 90 ° C to 110 ° C,From the first drop of water began to reflux for 4 hours.During the reaction, the lower water layer of the water separator was continuously released and measured with a graduated cylinderWater quantity.After the esterification reaction, the excess toluene and ethanol were distilled off under reduced pressure,The reaction product is then distilled under reduced pressure to give tributyl citrate.After completion of the reaction,The product esterification rate was 96.3percentThe yield of tributyl citrate was 84.4percent.
Reference：
[1] Tetrahedron, 2006, vol. 62, # 2-3, p. 422 - 433
[2] RSC Advances, 2018, vol. 8, # 66, p. 37835 - 37840
[3] Angewandte Chemie - International Edition, 2009, vol. 48, # 1, p. 168 - 171
[4] Green Chemistry, 2014, vol. 16, # 11, p. 4649 - 4653
[5] Patent: CN104447306, 2016, B, . Location in patent: Paragraph 0044-0048; 0052
[6] Patent: EP1491523, 2004, A1, . Location in patent: Page 16
[7] RSC Advances, 2014, vol. 4, # 100, p. 57297 - 57307
[8] Patent: CN106278881, 2017, A, . Location in patent: Paragraph 0017; 0018
[9] Archives of Biochemistry, 1950, vol. 28, p. 274,275
[10] Industrial and Engineering Chemistry, 1955, vol. 47, p. 797
[11] Journal of Pharmacy and Pharmacology, 1950, vol. 2, p. 229
[12] Bulletin of the Chemical Society of Ethiopia, 2011, vol. 25, # 1, p. 147 - 150
2
[ 109-69-3 ]
[ 68-04-2 ]
[ 77-94-1 ]
Reference：
[1] Patent: CN105237396, 2016, A, . Location in patent: Paragraph 0017
8.6 g of chlorobutane and 15.42 g of potassium iodide were added to 300 ml of acetone solution under reflux under nitrogen atmosphere for 2 hours. After completion of the reaction, the solvent of the reaction system was removed by distillation under reduced pressure. 20 g of <strong>[68-04-2]sodium citrate</strong> and 500 ml Of N, N-dimethylformamide was added to the reaction vessel. Then heated to 60 C and maintained at this temperature for 3 hours. After completion of the reaction, the solution was cooled to room temperature, and the reaction was washed three times with 2000 ml of deionized water. The organic phase was collected and the organic layer was dried over anhydrous sodium sulfate. After drying, the organic phase was allowed to warm to 50 C and the organic phase was distilled at this temperature for 2 hours using a vacuum distillation apparatus. The remaining liquid is tri-n-butyl citrate. Purity ? 95%, moisture <0.5%, heavy metals ? 0.0001%.
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