Synthesis of Polyethylene Glycol Vitamin E Succinate in Ionic Liquid

doi:10.11944/j.issn.1000-0518.2015.06.140366

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (6): 652-657.DOI: 10.11944/j.issn.1000-0518.2015.06.140366

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Synthesis of Polyethylene Glycol Vitamin E Succinate in Ionic Liquid

GONG Kai^*, WANG Liguo, CHEN Jinghua

School of Pharmaceutical Science,Jiangnan University,Wuxi,Jiangsu 214122,China

Received:2014-10-23 Accepted:2015-01-13 Published:2015-06-10 Online:2015-06-10
Contact: Kai GONG
Supported by:
Supported by the National Natural Science Foundation of China(No.51303069)

Abstract

Abstract:

Polyethylene glycol 1000(PEG 1000) Vitamin E succinate was prepared by a two-step esterification reaction of Vitamin E using ionic liquids as reaction catalysts. Vitamin E succinate(TAS) was obtained via the esterification of vitamin E catalyzed by 1-(N',N'-dimethylamino-ethyl)-3-methyl-imidazolium tetrafluoroborate. Under the conditions of 1:1.2 molar ratio of Vitamin E and succinic anhydride in 1,2-dichloroethane at 80 ℃ for 4 h, the isolated yield reached 90%. Under 1:2 molar ratio of TAS and PEG 1000 for 5 h at 100 ℃, polyethylene glycol 1000 Vitamin E succinate was synthesized in 1-methyl-3-propyl sulfonic acid imidazolium hydrogen sulfate/toluene media with 91% yield.

Key words: ionic liquid, green catalysis, vitamin E succinate, polyethylene glycol 1000 vitamin E succinate

CLC Number:

GONG Kai, WANG Liguo, CHEN Jinghua. Synthesis of Polyethylene Glycol Vitamin E Succinate in Ionic Liquid[J]. Chinese Journal of Applied Chemistry, 2015, 32(6): 652-657.

References

[1]	YU Yongxin,YU Hongkai,WANG Zhongyan. Advancement in Application of D-α-tocopherol Polyethylene Glycol 1000 Succinate[J]. J Shenyang Pharm Univ,2006,23(6):407-412(in Chinese). 于永新,俞红凯,王中彦. 聚乙二醇1000维生素E琥珀酸酯应用进展[J]. 沈阳药科大学学报,2006,23(6):407-412.
[2]	Guo Y Y,Luo J,Tan S W,et al.The Applications of Vitamin E TPGS in Drug Delivery[J]. Eur J Pharm Sci,2013,49(2):175-186.
[3]	Zhao J,Feng S S. Effects of PEG Tethering Chain Length of Vitamin E TPGS with a Herceptin-Functionalized Nanoparticle Formulation for Targeted Delivery of Anticancer Drugs[J]. Biomaterials,2014,35(10):3340-3347.
[4]	SUN Qian. The Synthesis and Purification of d-α-Tacopherol Succinate[D]. Hangzhou:Zhejiang University,2007(in Chinese). 孙倩. d-α-生育酚琥珀酸酯制备精制工艺研究[D]. 杭州:浙江大学,2007.
[5]	ZHENG Yansheng,SU Hui,LI Junsheng. Study on the Catalytic Synthesis of Vitamin E Succinate by Triethyl Amine[J]. Speciality Petrochem,2006,2(5):39-43(in Chinese). 郑燕升,粟晖,李军生. 三乙胺催化合成维生素E琥珀酸单酯的研究[J]. 精细石油化工,2006,2(5):39-43.
[6]	YI Yafei,WAND Yubiao,LIANG Qiyong. Synthesis of Tocopherol Calcium Succinate[J]. Chinese J Pharmaceut,1996,2:59-60(in Chinese). 冀亚飞,王玉标,梁启勇. 维生素E琥珀酸钙的合成[J]. 中国医药工业杂志,1996,2:59-60.
[7]	Tetsuya N,Saitama,Shizumasa K. Method of Producing α-Tacopherol Acid Succinate:US 3459774[P],1969-08-05.
[8]	WANG Jingyuan. The Preparation of d-α-Tocopheryl Polyethylene Glycol Succinate[D]. Hangzhou:Zhejiang University,2010(in Chinese). 王靖媛. d-α-生育酚聚乙二醇琥珀酸酯制备工艺研究[D]. 杭州:浙江大学,2010.
[9]	Collnot E M,Baldes C,Wempe M F,et al.Influence of Vitamin E TPGS Poly(ethylene glycol) Chain Length on Apical Efflux Transporters in Caco-2 Cell Monolayers[J]. J Control Release,2006,111(1/2):35-40.
[10]	Hallett J P,Welton T. Room-temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2[J]. Chem Rev,2011,111(5):3508-3576
[11]	SUN Jian,WANG Jinquan,ZHANG Suojiang,et al.Ionic Liquids Catalyzed Green Processes[J]. Sci Sin Chim,2014,44(1):100-113(in Chinese). 孙剑,王金泉,张锁江,等. 基于离子液体的绿色催化过程[J]. 中国科学:化学,2014,44(1):100-113.
[12]	Manoj K Muthyala,Kavya Velisetti,et al.Advances in Functionalized Ionic Liquids as Reagents and Scavengers in Organic Synthesis[J]. Curr Org Chem,2014,18(19):2530-2554.
[13]	GONG Kai,FANG Dong,LIU Zuliang. Catalyzed Synthesis of Substituted 2-Amino-2-Chromaenes by Functionalized Ionic Liquid[J]. Chinese J Appl Chem,2008,25(7):843-847(in Chinese). 巩凯,方东,刘祖亮. 功能化离子液体催化合成2-氨基-2-色烯衍生物[J]. 应用化学,2008,25(7):843-847.
[14]	Gong K,Fang D,Wang H L,et al.Eco-friendly and Efficient One-pot Synthesis of 14-Alkyl- or aryl-14H-dibenzo [a,j] xanthenes Catalyzed by Task-specific Ionic Liquid[J]. Dyes Pigm,2009,80(1):30-33.
[15]	FANG Dong,LIU Zuliang,ZHOU Xinli. Catalytic Synthesis of Benzyl Acetate in Task-specific Room Temperature Ionic Liquid[J]. Chinese J Appl Chem,2007,24(1):85-90(in Chinese). 方东,刘祖亮,周新利. 功能化离子液体室温催化合成乙酸苄酯[J]. 应用化学,2007,24(1):85-90.
[16]	Gu Y L,Shi F,Deng Y Q. Esterification of Aliphatic Acids with Olefin Promoted by Brønsted Acidic Ionic Liquids[J]. J Mol Catal A:Chem,2004,212(1/2):71-75.

Synthesis of Polyethylene Glycol Vitamin E Succinate in Ionic Liquid

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