Production Method 1

616-47-7

21228-90-0

45470-32-4

Reaction Conditions

1.1 10 °C

Reference

Preparation of sulfonate-ionic liquid with low halide content using microreactor

, Korea, , ,

Production Method 2

616-47-7

21228-90-0

45470-32-4

Reaction Conditions

1.1 Solvents: Toluene ;  < 40 °C; 1 h, rt

Reference

Synthesis of salidroside analog 4,4-di(4-hydroxyphenyl)pentyl-β-D-glucopyranoside

, China, , ,

Production Method 3

616-47-7

21228-90-0

45470-32-4

Reaction Conditions

1.1 Solvents: Toluene ;  0 °C; < 40 °C; 1 h, rt

Reference

Efficient, halide free synthesis of new, low cost ionic liquids: 1,3-dialkylimidazolium salts containing methyl- and ethyl-sulfate anions

Holbrey, John D.; Reichert, W. Matthew; Swatloski, Richard P.; Broker, Grant A.; Pitner, William R.; et al, Green Chemistry, 2002, 4(5), 407-413

Production Method 4

616-47-7

21228-90-0

45470-32-4

Reaction Conditions

Reference

A mild and efficient procedure for alkenols oxyselenocyclization by using ionic liquids

Kostic, Marina; Verdia, Pedro; Fernandez-Stefanuto, Veronica; Puchta, Ralph ; Tojo, Emilia, Journal of Physical Organic Chemistry, 2019, 32(5),

Production Method 5

21228-90-0

45470-32-4

Reaction Conditions

Reference

Preparation of ionic fluids by treatment of amines, phosphines, imidazoles, pyridines, triazoles, and pyrazoles with dialkyl sulfates followed by ion exchange.

, European Patent Organization, , ,

Production Method 6

75-93-4

118450-60-5

21228-90-0

45470-32-4

Reaction Conditions

1.1 Solvents: Toluene ;  0 °C

Reference

Electrosynthesis and electrochemical characterisation of polypyrrole in 1-hexyl-2,3-dimethylimidazolium tetrafluoroborate and 1,2-dimethylimidazolium methylsulfate. Application to the detection of copper in aqueous solutions

Dieye, El Hadji; Fall, Alioune; Fall, Modou ; Ferreira, Carlos Arthur ; Silveira, Mauro R. S. ; et al, International Journal of Environmental Analytical Chemistry, 2022, 102(17), 5166-5178

Production Method 7

616-47-7

21228-90-0

45470-32-4

Reaction Conditions

1.1 20 min, 0 °C; 120 min, 0 °C

Reference

Chloroperoxidase from Caldariomyces fumago is active in the presence of an ionic liquid as co-solvent

Sanfilippo, Claudia; D'Antona, Nicola; Nicolosi, Giovanni, Biotechnology Letters, 2004, 26(23), 1815-1819

Production Method 8

616-47-7

21228-90-0

45470-32-4

Reaction Conditions

1.1 Solvents: Toluene ;  rt; cooled; 20 - 30 °C; 2 h, rt

Reference

Method for preparing dialkylimidazolium bis(trifluoromethanesulfonyl)imide as electrolyte additive of lithium-ion battery

, China, , ,

Production Method 9

616-47-7

21228-90-0

45470-32-4

Reaction Conditions

1.1 48 h, rt

Reference

Volumetric Properties of Aqueous Ionic-Liquid Solutions at Different Temperatures

Shekaari, Hemayat; Zafarani-Moattar, Mohammed Taghi; Kazempour, Amir; Ghasedi-Khajeh, Zakiyeh, Journal of Chemical & Engineering Data, 2015, 60(6), 1750-1755

Production Method 10

616-47-7

21228-90-0

45470-32-4

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  rt; 24 h, 70 °C

Reference

1H NMR Evaluation of Polar and Nondeuterated Ionic Liquids for Selective Extraction of Cellulose and Xylan from Wheat Bran

Kuroda, Kosuke; Kunimura, Haruhito; Fukaya, Yukinobu; Nakamura, Nobuhumi; Ohno, Hiroyuki, ACS Sustainable Chemistry & Engineering, 2014, 2(9), 2204-2210

Production Method 11

616-47-7

21228-90-0

45470-32-4

Reaction Conditions

1.1 Solvents: Toluene ;  < 40 °C; 1 h, rt
1.2 Catalysts: Sulfuric acid ,  Water ;  rt → 70 °C

Reference

Alkyl Chain Interaction at the Surface of Room Temperature Ionic Liquids: Systematic Variation of Alkyl Chain Length (R = C1-C4, C8) in both Cation and Anion of [RMIM][R-OSO3] by Sum Frequency Generation and Surface Tension

Santos, Cherry S.; Baldelli, Steven, Journal of Physical Chemistry B, 2009, 113(4), 923-933

Production Method 12

616-47-7

21228-90-0

45470-32-4

Reaction Conditions

1.1 Solvents: Toluene ;  cooled; 1 h, rt

Reference

Removal of Organic Sulfur from Hydrocarbon Resources Using Ionic Liquids

Mochizuki, Yuuki; Sugawara, Katsuyasu, Energy & Fuels, 2008, 22(5), 3303-3307

Production Method 13

616-47-7

21228-90-0

45470-32-4

Reaction Conditions

1.1 Solvents: Toluene ;  rt; 2 h, rt

Reference

Study on preparation of room-temperature ionic liquids 1-alkyl-3-methylimidazole methyl sulfate and its electrical conductivity investigation

Yang, Xu-zhao; Wang, Jun; Li, Gang-sen; Zhang, Zhen-zhen, Jingxi Yu Zhuanyong Huaxuepin, 2007, 15(10), 16-18

Production Method 14

21228-90-0

45470-32-4

Reaction Conditions

Reference

Preparation of quaternary ammonium salt ionic liquid free of halogen ions and Na ions

, China, , ,

Production Method 15

21228-90-0

45470-32-4

Reaction Conditions

Reference

A simple, efficient and green procedure for Knoevenagel reaction in [MMIm][MSO4] ionic liquid

Santamarta, F.; Verdia, P.; Tojo, E., Catalysis Communications, 2008, 9(8), 1779-1781

Production Method 16

6596-81-2

21228-90-0

14996-02-2

45470-32-4

Reaction Conditions

1.1 Reagents: Hydrogen peroxide Solvents: Methanol

Reference

Thiono compounds. 5. Preparation and oxidation of some thiono derivatives of imidazoles

Karkhanis, Dattatraya W.; Field, Lamar, Phosphorus and Sulfur and the Related Elements, 1985, 22(1), 49-57

[(Sulfuric acid methyl)ion] Raw materials

• Sulfuric acid,monomethyl ester
• 1-Methylimidazole
• 1,3-dimethylimidazole-2(3h)-thione
• 1H-Imidazole, 2,3-dihydro-1,3-dimethyl-

[(Sulfuric acid methyl)ion] Preparation Products

• Sulfate, hydrogen(8CI,9CI) (14996-02-2)
• 1,3-Dimethylimidazolium (45470-32-4)
• [(Sulfuric acid methyl)ion] (21228-90-0)

• 1. Ester-mediated peptide formation promoted by deep eutectic solvents: a facile pathway to proto-peptides?
  Chen-Yu Chien,Sheng-Sheng Yu Chem. Commun., 2020,56, 11949-11952
• 2. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
  Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341
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  Joseph H. Bisesi,Tara Sabo-Attwood Environ. Sci.: Nano, 2014,1, 574-583
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  Analyst, 1880,5, 146-147
• 5. Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration?
  Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755

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