超声辐射下酸性离子液体催化合成1,1-二乙酸酯

doi:10.13218/j.cnki.csdc.2014.12.155

Abstract

Abstract: Under conditions of room temperature,solvent-free and ultrasonic irradiation,with an aromatic aldehyde and acetic anhydride as starting materials and functionalized acidic ionic liquid [C₃SO₃Hnhm][HSO₄] as catalyst,1,1-diacetates was synthesized.The optimal reaction conditions were found by single factor experiments.Reusing performance of the catalyst as well as applicability of the substrate were investigated.Results showed that when the molar ratio of benzaldehyde and acetic anhydride is 1:2.3;the reaction temperature is 20 ℃;ultrasonic irradiation applies for 15 min;and the dosage of catalyst is 1% of benzaldehyde;the yield can reach more than 96%.The catalyst [C₃SO₃Hnhm][HSO₄] can be reused for 5 times with no significant declining of the catalytic activity.In case the catalyst [C₃SO₃Hnhm][HSO₄] is used to catalyze the reaction of other aromatic aldehydes,the yield achieves 84%-98%.

Key words: 1,1-diacetate, acidic ionic liquid, ultrasonic irradiation, catalytic synthesis, green technology

CLC Number:

TQ655

TANG Xiao-fang, LIU Xian-ming, ZHOU Hao, CHOU Tao-tao, CHU Hai-rong, XING Zhi-heng. Synthesis of 1,1-diacetates with acidic ionic liquid as catalyst under ultrasonic irradiation[J].China Surfactant Detergent & Cosmetics, 2014, 44(12): 695-699.

References

[1] SYDNES L K,SANDBERG M.The reactivity of acylals towards grignard and organolithium reagents [J].Tetrahedron Lett,1997,53(37):12679-12690.
[2] FREEMAN F,KARCHEFSKI E M.Preparation and spectral properties of benzylidene diacetates [J].Chem Eng Data,1977,22(3):355-357.
[3] YADAV J S,REDDY B V S,SRINIVAS C.Indium trichloride catalyzed chemoselective conversion of aldehydes to gem-diacetates [J].Synth Commun,2002,32(5):2149-2153.
[4] SATYA V,RAJU N,SULFATED Z.An efficient catalyst for the sythesis of 1,1-diacetates from aldehydes and ketones [J].Chem Res,1996,26(3):68-69.
[5] BABAK K,HASSAN S,EBRAHIMIAN G R.Mild and efficient conersion of aldehydes to 1,1-diacetates catalyzed with N-bromosucci-nimide (NBS) [J].Synlett,2000,22(5):623-624.
[6] NABBJYOTI D,DIPOK J K,RULI B,et al.Locling as acetylation catalyst in the preparation of 1,1-diacetates from aldehydes [J].Org Chem,1997,62(3):1563-1564.
[7] MAJID M H,HADIJED B,SHIMA T,et al.KHSO₄:A catalyst for the chem-selective preparation of 1,1-diacetates from aldehydes under solvent-free conditions [J].Green Chemistry,2005,29(7):867-869.
[8] GUSTAVO P R,HORACIO J T,GRACIELA T B,et al.Solvent-free catalytic preparation of 1,1-diacetates from aldehydes using a wells-dawson acid (H₆P₂W₁₈O₆₂·24H₂O) [J].Tetrahedrom Letters,2003,44(1):1301-1303.
[9] 李成,张鹏辉,高书涛,等.功能化酸性离子液体[HSO₃-ppy][CF₃COOH]催化1,1-二乙酸酯的绿色合成[J].河北农业大学学报,2013,36(3):107-109,114.
[10] WEITON T.Room-temperature ionic liquids solvent for synthesis and catalysis [J].Chem Rev,1999,99(8):2071-2803.
[11] DUPONT J D,SOUZA R F,SUAREZ P A Z.Ionic liquid (molten salt) phase organometallic catalysis [J].Chem Rev,2002,102(10):3667-3692.
[12] JAIN N,KUMAR A,CHAUHAN S,et al.Chemical and biochemical transformations in ionic liquids [J].Tetrahedron,2005,61(5):1015-1060.
[13] CHOWDHURY S,MOHAN R S,SCOTT J L.Reactivity of ionic liquids [J].Tetrahedron,2007,63(11):2363-2389.
[14] 汤小芳,冯雷,祁贵国.硅胶固载[HSO₃-Pmim][HSO₄]催化合成对羟基苯甲酸乙酯[J].日用化学工业,2013,43(6):441-444.
[15] 黄宝华,黎字进,史娜,等.吗啡啉功能化酸性离子液体的合成、表征及其催化酯化性能[J].有机化学,2009,29(5):770-775.
[16] 余意,郭红云.无溶剂条件下离子液体[HNMP]HSO₄催化一锅法合成2′-氨基苯并噻唑-芳甲基-2-萘酚[J].有机化学,2011,31(1):96-100.
[17] ZHANG J,BAO S H,YANG J G.Synthesis of a novel multi-SO₃H functionalized strong Brnsted acidic ionic liquid and its catalytic activities for acetalization [J].Chinese Science Bulletin,2009,54(21):3958-3964.
[18] FREEMAN F,KARCHEFSKI E M.Preparation and spectral properties of benzylidene diacetates [J].Org Chem,1983,48(12):1765-1767.

Synthesis of 1,1-diacetates with acidic ionic liquid as catalyst under ultrasonic irradiation

PDF (PC)

Like

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 6

Metrics

Comments

Recommended 10

[1]	TANG Xiao-fang, LIU Xian-ming, ZHOU Si-yan, LI Shuang. Synthesis of benzoxanthene catalyzed by functionalized ionic liquids [C₃SO₃Hnhm]HSO₄ [J]. China Surfactant Detergent & Cosmetics, 2018, 48(11): 627-631.
[2]	XIANG Shi-yin, YANG Shui-jin. Preparation of H₆P₂Mo₉W₉O₆₂/Cu₃(BTC)₂ and its catalytic performance for synthesis of acetals and ketals [J]. China Surfactant Detergent & Cosmetics, 2017, 47(5): 281-285.
[3]	YUE Jin-fang,LUO Zhi-chen,DING Yi,WANG Xue-lan. Study on the synthesis of cinnamic acid catalyzed by KF/K₂CO₃/γ-Al₂O₃ under ultrasonic irradiation [J]. China Surfactant Detergent & Cosmetics, 2016, 46(7): 400-403.
[4]	DU Bin,LUO Zhi-chen,DING Yi,WANG Chen. Synthesis of dodecyl glycidyl ether under ultrasonic irradiation by phase transfer catalysis [J]. China Surfactant Detergent & Cosmetics, 2016, 46(11): 634-637.
[5]	LIU Qun,DING Bin,GUAN Chang,WANG Hai-dong,LI Xiang,HAO Feng-ling. Kinetics of synthesis of octyl acetate [J]. China Surfactant Detergent & Cosmetics, 2016, 46(1): 8-12.
[6]	ZENG Yu-cai, LIU Xiao-ling, LI Lan. Synthesis and spectroscopic property of 6-phenylazo-coumarin- 3-ethyl formate catalyzed by potassium carbonate [J]. China Surfactant Detergent & Cosmetics, 2014, 44(9): 512-516.