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ChemicalBook CAS DataBase List 4-HYDROXYMETHYL-1,3-DIOXOLAN-2-ONE
931-40-8

4-HYDROXYMETHYL-1,3-DIOXOLAN-2-ONE synthesis

10synthesis methods
A stirred mixture of potassium hydrogen carbonate (10.0 g, 0.1 mol), 18-crown-6 (0.2 g, 0.76 mmol), and 1-chloro-2,3-epoxypropane (27.6 g, 0.3 mol) was heated at 80℃ for 36 h. After cooling and removal of the potassium salt by filtration, the organic layer was washed with water and 991 was distilled at 152–160℃/0.6–0.8 mmHg; yield 4.83 g (41%).
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Yield:931-40-8 100%

Reaction Conditions:

Candida antarctica lipase B in tert-butyl alcohol at 70; for 10 - 24 h;Enzyme kinetics;Enzymatic reaction;Molecular sieve;

Steps:

1; 2; 3
Based on the first estimation, mean values and a conversion ratio and yield with respect to each factor as shown in Table 2 below were measured in a case where the reaction temperature was about 70 °C, t-BuOH was used as the reaction solvent, and a molecular sieve (M.Sieve) was additionally contained in the reaction solvent. Similar to the first estimation, in order to produce a mean value of the combination of all factors for each level, a total of 27 data was produced. Meanwhile, an amount of the catalyst was determined to have a concentration of about 0.5 % or more based on the first estimation results.[Table 2]FIG. 4 is a graph showing a mean value of a conversion ratio with respect to changes in a catalyst concentration, a molecular sieve concentration, and a reaction time according to an exemplary embodiment of the invention, and FIG. 5 is a graph showing a mean value of a yield (%) with respect to changes in a catalyst concentration, a molecular sieve concentration, and a reaction time according to an exemplary embodiment of the invention. Referring to FIGS. 4 and 5, when the molecular sieve is used, both of the conversion ratio and yield increase. Also, the conversion ratio becomes nearly saturated for about 5 hours, however the yield continuously increases over time. Also, the conversion ratio and yield increase along with an increase in the concentration of the molecular sieve. FIG. 6 is a graph showing changes in a conversion ratio and yield over time with respect to all combinations of a catalyst concentration and molecular sieve concentration according to an exemplary embodiment of the invention.Referring to FIG. 6, the conversion ratio becomes nearly saturated when exceeding about 5 hours, however the yield continuously increases. Also, the increase in the yield is also dramatically slowed after about 10 hours. Accordingly, maintaining the reaction time for about 10 hours may be effective in view of the processing efficiency.Also, in the second estimation, the conversion ratio and yield are maximized when the reaction is performed under the concentration of catalyst of about 1.0 % and the concentration of molecular sieve of about 500 wt.% relative to a weight of glycerol. Accordingly, in view of experimental errors, the yield may be maximized when the concentration of catalyst is about 0.8 % to 1.2 % and an amount of molecular sieve is about 450 to 550 parts by weight relative to about 100 parts by weight of the glycerol.As described above, in view of the processing efficiency, the reaction time may be preferably within about 24 hours, and more preferably about 10 hours. GC synthesis using crude glycerolA crude glycerol of two companies having a composition shown in Table 3 below was used as a starting material. GC was synthesized according to experimental conditions shown in Table 4 below and a conversion ratio and yield was estimated. [Table 3][Table 4] FIG. 7 is a graph showing changes in a conversion ratio and yield over time as results of GC synthesis of two companies having a composition of Table 3 using a crude glycerol according to an exemplary embodiment of the invention.Referring to FIG. 7, the conversion ratio and yield are higher in a case of using the crude glycerol than those in a case of using the refined glycerol. This is because the glycerol may be generated as a byproduct according to the reaction of the crude glycerol.Also, the conversion ratio and yield becomes semi-saturated when exceeding about 5 hours, and then a gentle increase in the conversion ratio and yield is shown. On a basis of about 10 hours, the conversion ratio and yield are respectively about 91.0 % and 97.5 % when using the crude glycerol of the company A. Also, the conversion ratio and yield are respectively about 86.0 % and 103.6 % when using the crude glycerol of the company B.Accordingly, the conversion ratio and yield when using the crude glycerol are relatively higher in comparison with when using the refined glycerol.

References:

GS CALTEX CORPORATION WO2009/35269, 2009, A2 Location in patent:Page/Page column title page; 6-9; 4/7 - 7/7

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