Abstract: 1-(3-Sulfonic acid)propyl-3-ethylimidazole hydrogen sulfate BAIL, a sulfonic acid-based functionalized ionic liquid, is synthesized through a two-step reaction method, and its structure is characterized by 1H-NMR.The ionic liquid is used to catalyze the esterification reaction between mercaptopropionic acid and methanol to synthesize methyl 3-mercaptopropionate.The effects of reaction temperature, the molar ratio of mercaptopropionic acid to methanol, and the addition amount of catalyst BAIL on the esterification reaction are discussed.It is shown that BAIL exhibits a good catalytic activity for the synthesis of methyl 3-mercaptopropionate.The conversion rate of mercaptopropionic acid can reach as high as 93.2% under the optimal conditions that n(CH3OH):n(MPA)=2:1, the reaction time is 1.5 h, and the reaction temperature is at 70℃, and the amount of catalyst is 10% that of mercaptopropionic acid.The catalyst has a good stability and maintains high activity after 5 times of repeated use.
杨红军, 李军峰, 毛志鹏, 陈建. 磺酸基离子液体催化合成3-巯基丙酸甲酯的研究[J]. 现代化工, 2022, 42(5): 202-205.
YANG Hong-jun, LI Jun-feng, MAO Zhi-peng, CHEN Jian. Synthesis of methyl 3-mercaptopropionate catalyzed by sulfonic acid-based ionic liquid. Modern Chemical Industry, 2022, 42(5): 202-205.
[1] 姜旭.巯基化合物的合成研究[D].成都:四川大学, 2004. [2] 刘玉生.3-巯基丙酸甲酯的绿色合成[J].精细与专用化学品, 2019, 27(6):19-21. [3] 北京天擎化工有限公司.3-巯基丙酸酯的制备:CN201110059175.6[P].2012-09-19. [4] Soleimani O.Properties and applications of ionic liquids[J].Journal of Chemical Reviews, 2020, 2(3):169-181. [5] Zhao H, Malhotra S V.Applications of ionic liquids in organic synthesis[J].Aldrichumica Acta, 2002, 35(3):75-83. [6] Tundo P, Anastas P, Black D S C, et al.Special topic issue on green chemistry[J].Pure Appl Chem, 2000, 72(7):1207-1228. [7] Hallett J P, Welton T.Room-temperature ionic liquids:Solvents for synthesis and catalysis.2[J].Chemical Reviews, 2011, 111(5):3508-3576. [8] Palacio M, Bhushan B.A review of ionic liquids for green molecular lubrication in nanotechnology[J].Tribology Letters, 2010, 40(2):247-268. [9] Cole A C, Jensen J L, Ntai I, et al.Novel Brønsted acidic ionic liquids and their use as dual solvent-catalysts[J].Journal of the American Chemical Society, 2002, 124(21):5962-5963. [10] Fraga-Dubreuil J, Bourahla K, Rahmouni M, et al.Catalysed esterifications in room temperature ionic liquids with acidic counteranion as recyclable reaction media[J].Catalysis Communications, 2002, 3(5):185-190. [11] Gui J, Cong X, Liu D, et al.Novel Brønsted acidic ionic liquid as efficient and reusable catalyst system for esterification[J].Catalysis Communications, 2004, 5(9):473-477. [12] Xing H, Wang T, Zhou Z, et al.Novel Brønsted-acidic ionic liquids for esterifications[J].Industrial & Engineering Chemistry Research, 2005, 44(11):4147-4150. [13] Li X, Eli W, Li G.Solvent-free synthesis of benzoic esters and benzyl esters in novel Brønsted acidic ionic liquids under microwave irradiation[J].Catalysis Communications, 2008, 9(13):2264-2268. [14] Li X, Eli W.A green approach for the synthesis of long chain aliphatic acid esters at room temperature[J].Journal of Molecular Catalysis A:Chemical, 2008, 279(2):159-164. [15] Zhao Y, Long J, Deng F, et al.Catalytic amounts of Brønsted acidic ionic liquids promoted esterification:Study of acidity-activity relationship[J].Catalysis Communications, 2009, 10(5):732-736. [16] Liu X, Ma H, Wu Y, et al.Esterification of glycerol with acetic acid using double SO 3 H-functionalized ionic liquids as recoverable catalysts[J].Green Chemistry, 2011, 13(3):697-701. [17] Tao D J, Lu X M, Lu J F, et al.Noncorrosive ionic liquids composed of[HSO4] as esterification catalysts[J].Chemical Engineering Journal, 2011, 171(3):1333-1339. [18] Ouyang C, Feng S, Huo J, et al.Three-dimensional hierarchical MoS2/CoS2 heterostructure arrays for highly efficient electrocatalytic hydrogen evolution[J].Green Energy & Environment, 2017, 2(2):134-141. [19] Zeng Q, Song Z, Qin H, et al.Ionic liquid[BMIm] [HSO4] as dual catalyst-solvent for the esterification of hexanoic acid with n-butanol[J].Catalysis Today, 2020, 339:113-119. [20] Wei C, Rao R R, Peng J, et al.Recommended practices and benchmark activity for hydrogen and oxygen electrocatalysis in water splitting and fuel cells[J].Advanced Materials, 2019, 31(31):1806296. [21] Gui J, Cong X, Liu D, et al.Novel Brønsted acidic ionic liquid as efficient and reusable catalyst system for esterification[J].Catalysis Communications, 2004, 5(9):473-477.