Study on crystallization separation of ursolic acid and oleanolic acid in ionic liquid

doi:10.11949/0438-1157.20200003

Abstract

Abstract:

To expand the scope of crystallization solvent and improve the performance of crystallization separation of ursolic acid and oleanolic acid, ionic liquids were introduced as the crystallization solvent. The solubility data of ursolic acid and oleanolic acid in six ionic liquids + ethanol mixed solutions were measured. Then the 1-octyl-3-methylimidazole hexafluorophosphate + ethanol mixed solution was selected as the solvent for crystallization separation of ursolic acid and oleanolic acid, and the crystallization process was optimized by single factor experiments. The best process conditions are as follows: mass fraction of 1-octyl-3-methylimidazole hexafluorophosphat 5%, mass ratio of ursolic acid to oleanolic acid 1.5∶1, crystallization temperature 30℃, crystallization time 14 h. In this case, the mass fraction of oleanolic acid in the crystals can reach about 85%.

Key words: ursolic acid, oleanolic acid, ionic liquid, solubility, crystallization separation

摘要：

为拓展结晶溶剂的范围和提高结晶分离熊果酸和齐墩果酸的性能，引入离子液体作为结晶溶剂。测定了熊果酸和齐墩果酸在六种离子液体+乙醇溶液中的溶解度数据，根据该数据，选取1-辛基-3-甲基咪唑六氟磷酸+乙醇混合溶液作为溶剂对熊果酸和齐墩果酸进行了结晶分离，并采用单因素实验对结晶工艺进行了初步优化。结果表明：在1-辛基-3-甲基咪唑六氟磷酸质量分数5%，熊果酸和齐墩果酸质量比1.5∶1，结晶温度30℃，结晶时间14 h的条件下，结晶产物中齐墩果酸的质量分数可以达到85%左右。

关键词: 熊果酸, 齐墩果酸, 离子液体, 溶解度, 结晶分离

CLC Number:

TQ 028.8

Yi GAO, Yahui CAO, Jieping FAN. Study on crystallization separation of ursolic acid and oleanolic acid in ionic liquid[J]. CIESC Journal, 2020, 71(8): 3633-3643.

高意, 曹亚慧, 范杰平. 离子液体中结晶分离熊果酸和齐墩果酸研究[J]. 化工学报, 2020, 71(8): 3633-3643.

Figures/Tables 17

References 35

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T/K	A	B	C	D	E	F
293.2	2.58701	4.62446	3.91696	4.08962	4.21600	4.95054
298.2	3.29014	5.50223	4.81039	5.10499	5.29339	5.10910
303.2	6.43360	7.16866	5.35800	6.73191	7.45408	7.41121
308.2	7.26193	7.37772	5.73489	7.14156	7.94014	8.12856
313.2	7.76808	7.72152	6.34713	7.28522	8.14792	9.20341
318.2	9.23542	8.46756	9.97358	9.03714	8.20060	10.14640
323.2	11.99561	10.87394	11.60734	10.82879	9.76161	11.87940
328.2	13.93287	10.97432	12.10037	11.91585	11.95445	12.84131
333.2	14.36265	11.72096	13.70408	12.14856	14.51312	19.50879

T/K	A	B	C	D	E	F
293.2	2.58701	4.62446	3.91696	4.08962	4.21600	4.95054
298.2	3.29014	5.50223	4.81039	5.10499	5.29339	5.10910
303.2	6.43360	7.16866	5.35800	6.73191	7.45408	7.41121
308.2	7.26193	7.37772	5.73489	7.14156	7.94014	8.12856
313.2	7.76808	7.72152	6.34713	7.28522	8.14792	9.20341
318.2	9.23542	8.46756	9.97358	9.03714	8.20060	10.14640
323.2	11.99561	10.87394	11.60734	10.82879	9.76161	11.87940
328.2	13.93287	10.97432	12.10037	11.91585	11.95445	12.84131
333.2	14.36265	11.72096	13.70408	12.14856	14.51312	19.50879

T/K	A	B	C	D	E	F
293.2	3.66277	3.90568	3.18137	3.82803	4.55719	4.82319
298.2	4.11362	4.95578	4.31056	4.99628	5.06101	5.14561
303.2	5.06655	5.27193	4.72241	5.20969	5.64367	5.38338
308.2	5.48627	5.85894	5.47927	5.51890	6.01389	5.94459
313.2	7.41711	7.05214	6.22817	5.99910	7.70761	7.04455
318.2	8.12955	7.52216	6.90739	8.61030	8.26677	7.94869
323.2	8.32516	8.86441	7.81490	9.39422	9.87569	9.81278
328.2	9.94503	10.66226	10.42502	11.90057	10.83787	10.30029
333.2	12.56636	14.51072	13.08634	15.93602	15.17506	14.08778

T/K	A	B	C	D	E	F
293.2	3.66277	3.90568	3.18137	3.82803	4.55719	4.82319
298.2	4.11362	4.95578	4.31056	4.99628	5.06101	5.14561
303.2	5.06655	5.27193	4.72241	5.20969	5.64367	5.38338
308.2	5.48627	5.85894	5.47927	5.51890	6.01389	5.94459
313.2	7.41711	7.05214	6.22817	5.99910	7.70761	7.04455
318.2	8.12955	7.52216	6.90739	8.61030	8.26677	7.94869
323.2	8.32516	8.86441	7.81490	9.39422	9.87569	9.81278
328.2	9.94503	10.66226	10.42502	11.90057	10.83787	10.30029
333.2	12.56636	14.51072	13.08634	15.93602	15.17506	14.08778

溶剂体系	a	b	c	R²	RAD	RMSD×10⁴
A	692.52	-35383.00	-100.48	0.9653	0.0903	0.6476
B	190.14	-10580.53	-26.84	0.9470	0.0447	0.4667
C	152.68	-9827.87	-20.75	0.9429	0.0813	0.7159
D	272.51	-14774.22	-38.85	0.9638	0.0445	0.4517
E	-283.51	11096.12	43.53	0.9226	0.0861	0.7177
F	-613.83	25985.89	92.75	0.9359	0.0842	0.9308