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174501-64-5

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174501-64-5 Usage

Conductivity

1.92 mS/cm

Chemical Properties

Clear pale yellow oil

Uses

Different sources of media describe the Uses of 174501-64-5 differently. You can refer to the following data:
1. those consisting of tetrafluoroborate, alkylsulfate, alkylsulfonate, carboxylate, or phosphate anions are hydrophilic and are completely dissolved in water. Dupont and coworkers first reported stable hydrophobic imidazolium salt, 1-butyl-3-methylimidazolium hexafluorophosphate ([C4mim][PF6]) in 1996. Since then, this salt has been used as a typical hydrophobic IL in many chemical reactions because its mixture with water forms a biphasic layer. Furthermore, this IL shows poor solubility in hexane or ether, which allows realization of an easy work-up process. However, [C4mim][PF6] was reported to be sensitive to the moisture at high temperature and produced hazardous hydrogen fluoride as it decomposed. Therefore, bis(trifluoromethanesulfonyl)amide (NTf2) salts are now recommended as the anion for preparing hydrophobic ILs.
2. 1-Butyl-3-methylimidazolium hexafluorophosphate is an ionic liquid employed in many environmentally friendly reactions. It can also be used as a medium for reactions such as: Ring-closing metathesis of diene and enyne substrates in the presence of a novel recyclable ruthenium carbene complex.Nickel(II)acetylacetonate catalyzed oxidation of aromatic aldehydes to the corresponding acids using dioxygen as the oxidant.Lipase-catalyzed enantioselective acylation of allylic alcohols.Allylation of aldehydes using tetraallylstannane to yield homoallylic alcohols.

General Description

1-Butyl-3-methylimidazolium hexafluorophosphate is an imidazolium-based, hydrophobic, room temperature ionic liquid (RTIL). It can be prepared by reacting 1-methylimidazole with chlorobutane. Gaseous hydrofluorocarbons (HFCs) such as fluoromethane, fluoroethane and 1,1,2,2-tetrafluoroethane are soluble in BMIMPF6.

Check Digit Verification of cas no

The CAS Registry Mumber 174501-64-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,4,5,0 and 1 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 174501-64:
(8*1)+(7*7)+(6*4)+(5*5)+(4*0)+(3*1)+(2*6)+(1*4)=125
125 % 10 = 5
So 174501-64-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H16N2.F6P/c1-3-4-5-10-7-6-9(2)8-10;1-7(2,3,4,5)6/h6-7H,3-5,8H2,1-2H3;/q;-1/p+1

174501-64-5 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • TCI America

  • (B2320)  1-Butyl-3-methylimidazolium Hexafluorophosphate  >98.0%(HPLC)(N)

  • 174501-64-5

  • 5g

  • 280.00CNY

  • Detail
  • TCI America

  • (B2320)  1-Butyl-3-methylimidazolium Hexafluorophosphate  >98.0%(HPLC)(N)

  • 174501-64-5

  • 25g

  • 790.00CNY

  • Detail
  • Alfa Aesar

  • (L19086)  1-n-Butyl-3-methylimidazolium hexafluorophosphate, 98+%   

  • 174501-64-5

  • 5g

  • 858.0CNY

  • Detail
  • Alfa Aesar

  • (L19086)  1-n-Butyl-3-methylimidazolium hexafluorophosphate, 98+%   

  • 174501-64-5

  • 25g

  • 1786.0CNY

  • Detail
  • Alfa Aesar

  • (L19086)  1-n-Butyl-3-methylimidazolium hexafluorophosphate, 98+%   

  • 174501-64-5

  • 100g

  • 2518.0CNY

  • Detail
  • Sigma-Aldrich

  • (18122)  1-Butyl-3-methylimidazoliumhexafluorophosphate  for catalysis, ≥98.5% (T)

  • 174501-64-5

  • 18122-5G-F

  • 2,322.45CNY

  • Detail
  • Sigma-Aldrich

  • (18122)  1-Butyl-3-methylimidazoliumhexafluorophosphate  for catalysis, ≥98.5% (T)

  • 174501-64-5

  • 18122-50G-F

  • 14,660.10CNY

  • Detail
  • Aldrich

  • (70956)  1-Butyl-3-methylimidazoliumhexafluorophosphate  ≥97.0% (HPLC)

  • 174501-64-5

  • 70956-5G

  • 868.14CNY

  • Detail
  • Aldrich

  • (70956)  1-Butyl-3-methylimidazoliumhexafluorophosphate  ≥97.0% (HPLC)

  • 174501-64-5

  • 70956-50G

  • 2,127.06CNY

  • Detail
  • Aldrich

  • (70956)  1-Butyl-3-methylimidazoliumhexafluorophosphate  ≥97.0% (HPLC)

  • 174501-64-5

  • 70956-250G

  • 7,034.04CNY

  • Detail

174501-64-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Butyl-3-methylimidazolium hexafluorophosphate

1.2 Other means of identification

Product number -
Other names 1-butyl-3-methylimidazolium hexafluorophosphate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:174501-64-5 SDS

174501-64-5Synthetic route

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With Amberlyst A-26 (PF6- form) In methanol100%
With sodium hexaflorophosphate In acetone at 80℃; for 0.166667h; microwave irrradiation;99%
With potassium hexafluorophosphate In acetone at 20℃; for 24h;98%
1-n-butyl-3-methylimidazolim bromide
85100-77-2

1-n-butyl-3-methylimidazolim bromide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate In water at 20℃;100%
With ammonium hexafluorophosphate In water at 20℃; for 2h;91%
With potassium hexafluorophosphate In water at 20℃; for 24h;87%
1-methyl-3-(n-butyl)imidazolium iodide
65039-05-6

1-methyl-3-(n-butyl)imidazolium iodide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With Amberlyst A-26 (PF6- form) In methanol100%
With Amberlist A-26 BF6(-) form In methanol Ionic liquid;
1-Butylimidazole
4316-42-1

1-Butylimidazole

trimethyl orthoformate
149-73-5

trimethyl orthoformate

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With ammonium hexafluorophosphate Reagent/catalyst; Schlenk technique; Reflux;95%
With ammonium hexafluorophosphate at 110℃; for 17h; Reagent/catalyst; Inert atmosphere;88%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

1-bromo-butane
109-65-9

1-bromo-butane

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate at 40 - 120℃; for 0.166667h; microwave irradiation; sonication;94%
With potassium hexafluorophosphate at 80℃; for 3.5h;93%
With ammonium hexafluorophosphate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 80℃; for 15h;89%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

n-Butyl chloride
109-69-3

n-Butyl chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With sodium hexaflorophosphate at 70℃; for 336h;92%
Stage #1: 1-methyl-1H-imidazole; n-Butyl chloride In toluene for 48h; Reflux;
Stage #2: With potassium hexafluorophosphate In toluene
92%
With potassium hexafluorophosphate at 120 - 180℃; for 0.75h; microwave irradiation;90%
1-Butylimidazole
4316-42-1

1-Butylimidazole

dimethyl sulfate
77-78-1

dimethyl sulfate

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: 1-Butylimidazole; dimethyl sulfate for 0.25h;
Stage #2: With sodium hexaflorophosphate In water
92%
1-butyl-3-methylimidazolium chloride

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate In acetone for 24h;90%
methanol
67-56-1

methanol

N-methyl-N'-n-butylimidazolium-2-carboxylate
671779-18-3

N-methyl-N'-n-butylimidazolium-2-carboxylate

A

potassium monomethylcarbonate
14660-45-8

potassium monomethylcarbonate

B

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate at 20℃; for 12h;A 87%
B 72%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

1-iodo-butane
542-69-8

1-iodo-butane

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 80℃; for 10h;85%
ammonium hexafluorophosphate

ammonium hexafluorophosphate

1-n-butyl-3-methylimidazolim bromide
85100-77-2

1-n-butyl-3-methylimidazolim bromide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;75%
potassium fluoride

potassium fluoride

N-trimethylsilyl-tris(pentafluorethyl)phosphazen

N-trimethylsilyl-tris(pentafluorethyl)phosphazen

Trimethyl borate
121-43-7

Trimethyl borate

hydrogen fluoride
7664-39-3

hydrogen fluoride

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

A

1-methyl-3-n-butylimidazolium pentafluoroethyltrifluoroborate

1-methyl-3-n-butylimidazolium pentafluoroethyltrifluoroborate

B

1-methyl-3-butylimidazolium (pentafluoroethyl)pentafluorophosphate

1-methyl-3-butylimidazolium (pentafluoroethyl)pentafluorophosphate

C

1-methyl-3-butylimidazolium bis(pentafluoroethyl)tetrafluorophosphate

1-methyl-3-butylimidazolium bis(pentafluoroethyl)tetrafluorophosphate

D

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: potassium fluoride; N-trimethylsilyl-tris(pentafluorethyl)phosphazen; Trimethyl borate In 1,2-dimethoxyethane at 20 - 60℃; for 1h;
Stage #2: hydrogen fluoride In 1,2-dimethoxyethane; water at 0 - 20℃; for 3h;
Stage #3: 1-butyl-3-methylimidazolium chloride In water
A 60%
B 30%
C 6%
D 4%
1-Butylimidazole
4316-42-1

1-Butylimidazole

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: 1-Butylimidazole; carbonic acid dimethyl ester In methanol at 135℃; for 7h;
Stage #2: With sodium hexaflorophosphate In methanol; acetone at 25℃; for 2h;
52%
1-Butylimidazole
4316-42-1

1-Butylimidazole

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 - 70 °C
2: NH4PF6
View Scheme
hexafluorophosphate anion

hexafluorophosphate anion

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
at 20℃;
formaldehyd
50-00-0

formaldehyd

Glyoxal
131543-46-9

Glyoxal

N-butylamine
109-73-9

N-butylamine

methylamine
74-89-5

methylamine

A

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

B

1,3-dimethyl-1H-imidazol-3-ium hexafluorophosphate

1,3-dimethyl-1H-imidazol-3-ium hexafluorophosphate

C

1,3-di-n-butylimidazolium hexafluorophosphate

1,3-di-n-butylimidazolium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: formaldehyd; N-butylamine; methylamine In water at 0℃;
Stage #2: With hexafluorophosphoric acid In water at 0℃;
Stage #3: Glyoxal In water at 0 - 20℃;
1-butyl-3-methylimidazolium halide

1-butyl-3-methylimidazolium halide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With sodium hexaflorophosphate
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

n-butyl halide

n-butyl halide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With alkali metal hexafluorophosphate at 150℃; for 0.5h; Microwave irradiation; Cooling; neat (no solvent);
potassium hexafluorophosphate
17084-13-8

potassium hexafluorophosphate

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
In water at 20℃; for 24h;
sodium hexaflorophosphate

sodium hexaflorophosphate

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
In water
Ionic liquid; Inert atmosphere;
1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With Amberlyst A-26 (PF6- form) In methanol100%
With sodium hexaflorophosphate In acetone at 80℃; for 0.166667h; microwave irrradiation;99%
With potassium hexafluorophosphate In acetone at 20℃; for 24h;98%
1-n-butyl-3-methylimidazolim bromide
85100-77-2

1-n-butyl-3-methylimidazolim bromide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate In water at 20℃;100%
With ammonium hexafluorophosphate In water at 20℃; for 2h;91%
With potassium hexafluorophosphate In water at 20℃; for 24h;87%
1-methyl-3-(n-butyl)imidazolium iodide
65039-05-6

1-methyl-3-(n-butyl)imidazolium iodide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With Amberlyst A-26 (PF6- form) In methanol100%
With Amberlist A-26 BF6(-) form In methanol Ionic liquid;
1-Butylimidazole
4316-42-1

1-Butylimidazole

trimethyl orthoformate
149-73-5

trimethyl orthoformate

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With ammonium hexafluorophosphate Reagent/catalyst; Schlenk technique; Reflux;95%
With ammonium hexafluorophosphate at 110℃; for 17h; Reagent/catalyst; Inert atmosphere;88%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

1-bromo-butane
109-65-9

1-bromo-butane

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate at 40 - 120℃; for 0.166667h; microwave irradiation; sonication;94%
With potassium hexafluorophosphate at 80℃; for 3.5h;93%
With ammonium hexafluorophosphate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 80℃; for 15h;89%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

n-Butyl chloride
109-69-3

n-Butyl chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With sodium hexaflorophosphate at 70℃; for 336h;92%
Stage #1: 1-methyl-1H-imidazole; n-Butyl chloride In toluene for 48h; Reflux;
Stage #2: With potassium hexafluorophosphate In toluene
92%
With potassium hexafluorophosphate at 120 - 180℃; for 0.75h; microwave irradiation;90%
1-Butylimidazole
4316-42-1

1-Butylimidazole

dimethyl sulfate
77-78-1

dimethyl sulfate

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: 1-Butylimidazole; dimethyl sulfate for 0.25h;
Stage #2: With sodium hexaflorophosphate In water
92%
1-butyl-3-methylimidazolium chloride

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate In acetone for 24h;90%
methanol
67-56-1

methanol

N-methyl-N'-n-butylimidazolium-2-carboxylate
671779-18-3

N-methyl-N'-n-butylimidazolium-2-carboxylate

A

potassium monomethylcarbonate
14660-45-8

potassium monomethylcarbonate

B

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate at 20℃; for 12h;A 87%
B 72%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

1-iodo-butane
542-69-8

1-iodo-butane

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 80℃; for 10h;85%
ammonium hexafluorophosphate

ammonium hexafluorophosphate

1-n-butyl-3-methylimidazolim bromide
85100-77-2

1-n-butyl-3-methylimidazolim bromide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;75%
potassium fluoride

potassium fluoride

N-trimethylsilyl-tris(pentafluorethyl)phosphazen

N-trimethylsilyl-tris(pentafluorethyl)phosphazen

Trimethyl borate
121-43-7

Trimethyl borate

hydrogen fluoride
7664-39-3

hydrogen fluoride

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

A

1-methyl-3-n-butylimidazolium pentafluoroethyltrifluoroborate

1-methyl-3-n-butylimidazolium pentafluoroethyltrifluoroborate

B

1-methyl-3-butylimidazolium (pentafluoroethyl)pentafluorophosphate

1-methyl-3-butylimidazolium (pentafluoroethyl)pentafluorophosphate

C

1-methyl-3-butylimidazolium bis(pentafluoroethyl)tetrafluorophosphate

1-methyl-3-butylimidazolium bis(pentafluoroethyl)tetrafluorophosphate

D

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: potassium fluoride; N-trimethylsilyl-tris(pentafluorethyl)phosphazen; Trimethyl borate In 1,2-dimethoxyethane at 20 - 60℃; for 1h;
Stage #2: hydrogen fluoride In 1,2-dimethoxyethane; water at 0 - 20℃; for 3h;
Stage #3: 1-butyl-3-methylimidazolium chloride In water
A 60%
B 30%
C 6%
D 4%
1-Butylimidazole
4316-42-1

1-Butylimidazole

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: 1-Butylimidazole; carbonic acid dimethyl ester In methanol at 135℃; for 7h;
Stage #2: With sodium hexaflorophosphate In methanol; acetone at 25℃; for 2h;
52%
1-Butylimidazole
4316-42-1

1-Butylimidazole

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 - 70 °C
2: NH4PF6
View Scheme
hexafluorophosphate anion

hexafluorophosphate anion

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
at 20℃;
formaldehyd
50-00-0

formaldehyd

Glyoxal
131543-46-9

Glyoxal

N-butylamine
109-73-9

N-butylamine

methylamine
74-89-5

methylamine

A

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

B

1,3-dimethyl-1H-imidazol-3-ium hexafluorophosphate

1,3-dimethyl-1H-imidazol-3-ium hexafluorophosphate

C

1,3-di-n-butylimidazolium hexafluorophosphate

1,3-di-n-butylimidazolium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: formaldehyd; N-butylamine; methylamine In water at 0℃;
Stage #2: With hexafluorophosphoric acid In water at 0℃;
Stage #3: Glyoxal In water at 0 - 20℃;
1-butyl-3-methylimidazolium halide

1-butyl-3-methylimidazolium halide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With sodium hexaflorophosphate
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

n-butyl halide

n-butyl halide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With alkali metal hexafluorophosphate at 150℃; for 0.5h; Microwave irradiation; Cooling; neat (no solvent);
potassium hexafluorophosphate
17084-13-8

potassium hexafluorophosphate

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
In water at 20℃; for 24h;
sodium hexaflorophosphate

sodium hexaflorophosphate

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
In water
Ionic liquid; Inert atmosphere;
3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

Conditions
ConditionsYield
With Amberlyst A-26 (Cl- form) In methanol100%
3,6-bis-(3,5-dimethyl-pyrazol-1-yl)-1,2,4,5-tetrazine
30169-25-6

3,6-bis-(3,5-dimethyl-pyrazol-1-yl)-1,2,4,5-tetrazine

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

6-(1-butyl-3-methyl-1,3-dihydroimidazol-2-ylidene)-6H-[1,2,4,5]tetrazin-3-one

6-(1-butyl-3-methyl-1,3-dihydroimidazol-2-ylidene)-6H-[1,2,4,5]tetrazin-3-one

Conditions
ConditionsYield
Stage #1: 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate With potassium carbonate In acetonitrile for 0.666667h; Heating;
Stage #2: 3,6-bis-(3,5-dimethyl-pyrazol-1-yl)-1,2,4,5-tetrazine In acetonitrile Heating; Further stages.;
99%
3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

1-butyl-3-methyl-1H-imidazole-2(3H)-thione
119393-94-1

1-butyl-3-methyl-1H-imidazole-2(3H)-thione

Conditions
ConditionsYield
Stage #1: 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; Electrolysis; Inert atmosphere;
Stage #2: With sulfur for 0.166667h; Inert atmosphere; Irradiation;
99%
3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

1-butyl-3-methyl-2-imidazolone
586965-19-7

1-butyl-3-methyl-2-imidazolone

Conditions
ConditionsYield
With superoxide radical anion at 25℃; under 742.574 Torr; Kinetics; Inert atmosphere;95%
AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)

AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

[Au(N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(BMIM)][PF6]

[Au(N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(BMIM)][PF6]

Conditions
ConditionsYield
In toluene byproducts: H2O; Au complex and (C3H3N2(CH3)C4H9)PF6 added to toluene, stirred at 25°C for 14 h; pptd. (pentane), collected on a frit, washed (pentane), dried (vac.); elem. anal.;95%
chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

1-butyl-2-(diphenylphosphanyl)-3-methylimidazolium hexafluorophosphate

1-butyl-2-(diphenylphosphanyl)-3-methylimidazolium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.75h; Metallation;
Stage #2: chloro-diphenylphosphine In tetrahydrofuran; hexane at -78℃; for 0.166667h; Substitution;
89%
Stage #1: 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate With n-butyllithium In hexane; dichloromethane at -78℃; for 1h;
Stage #2: chloro-diphenylphosphine In hexane; dichloromethane at -78 - 20℃;
88%
With n-butyllithium In hexane; dichloromethane at -78℃; for 1.08333h;84%
europium(III) chloride hexahydrate

europium(III) chloride hexahydrate

4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedione
893-33-4

4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedione

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

1-butyl-3-methylimidazolium tetrakis(naphthoyltrifluoroacetonato)europate(III)

1-butyl-3-methylimidazolium tetrakis(naphthoyltrifluoroacetonato)europate(III)

Conditions
ConditionsYield
With NaOH In ethanol; water (N2) soln. 1M NaOH was added to soln. ligand in EtOH at room temp., EuCl3*6H2O was added, stirred for 4 h at 50°C, evapd., residue was washed with hexane, dissolved in water, soln. (C4mim)Br in aq. EtOH was added, stirred for 1 h at room temp.; ppt. was filtered, washed with hexane, dried under vac.; elem. anal.;77%
carbon disulfide
75-15-0

carbon disulfide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

1-n-butyl-3-methylimidazolium-2-carbodithioate

1-n-butyl-3-methylimidazolium-2-carbodithioate

Conditions
ConditionsYield
Stage #1: 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere;
Stage #2: carbon disulfide In tetrahydrofuran at 20℃; for 0.5h; Mechanism; Inert atmosphere;
76%
terbium(III) nitrate pentahydrate

terbium(III) nitrate pentahydrate

acetylacetone
123-54-6

acetylacetone

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

[1-butyl-3-methylimidazolium ][Tb(acetylacetonate)4]

[1-butyl-3-methylimidazolium ][Tb(acetylacetonate)4]

Conditions
ConditionsYield
Stage #1: acetylacetone With sodium hydroxide In ethanol; water pH=8;
Stage #2: 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In ethanol; water at 50℃; for 0.5h;
Stage #3: terbium(III) nitrate pentahydrate In ethanol; water at 50℃; for 2h;
72%
carbon dioxide
124-38-9

carbon dioxide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

N-methyl-N'-n-butylimidazolium-2-carboxylate
671779-18-3

N-methyl-N'-n-butylimidazolium-2-carboxylate

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 100℃; under 60006 Torr; for 12h; Autoclave;70%
C4H4CuN4(1+)*F6P(1-)

C4H4CuN4(1+)*F6P(1-)

[BMIm]3[Nb6Cl12(NCS)6]

[BMIm]3[Nb6Cl12(NCS)6]

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

[BMIm][Nb6Cl12(SCN)6{Cu(CH3CN)}2]

[BMIm][Nb6Cl12(SCN)6{Cu(CH3CN)}2]

Conditions
ConditionsYield
In acetonitrile Inert atmosphere; Glovebox; Schlenk technique;41%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

iron pentacarbonyl
13463-40-6, 71564-23-3

iron pentacarbonyl

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

hexakis(1-methylimidazole)iron(II) hexafluorophosphate

hexakis(1-methylimidazole)iron(II) hexafluorophosphate

Conditions
ConditionsYield
In further solvent(s) byproducts: CO; Sonication; Fe complex and ligand dispersed in ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate, conicated at 40-50°C for 30 min (air); pptd.(ethanol), elem. anal., XRD;28%
3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

1-n-butyl-3-methyl-2,3-dihydro-imidazol-2-ylidene
366491-14-7

1-n-butyl-3-methyl-2,3-dihydro-imidazol-2-ylidene

Conditions
ConditionsYield
With n-butyllithium In hexane; dichloromethane at -78℃; for 1h;
With N,N,N,N-tetraethylammonium tetrafluoroborate In N,N-dimethyl-formamide at 25℃; Inert atmosphere; Electrolysis;
In N,N-dimethyl-formamide at 25℃; Inert atmosphere; Electrolysis;
3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

A

1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

B

1-butylene
106-98-9

1-butylene

C

1-fluorobutane
2366-52-1

1-fluorobutane

Conditions
ConditionsYield
With cesium fluoride at 150℃; for 96h;
furfural
98-01-1

furfural

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

A

methyl 2-(furan-2-yl(hydroxy)methyl)acrylate
87102-10-1

methyl 2-(furan-2-yl(hydroxy)methyl)acrylate

B

C13H19N2O2(1+)*F6P(1-)

C13H19N2O2(1+)*F6P(1-)

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 24h; Baylis-Hillman;
3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

A

3-butyl-2-fluoro-1-methyl-3H-imidazol-1-ium

3-butyl-2-fluoro-1-methyl-3H-imidazol-1-ium

B

3-[4-(1-butyl-3-methyl-2,3-dihydro-1H-imidazol-2-yl)-butyl]-1-methyl-3H-imidazol-1-ium

3-[4-(1-butyl-3-methyl-2,3-dihydro-1H-imidazol-2-yl)-butyl]-1-methyl-3H-imidazol-1-ium

C

1-methyl-3H-imidazolium

1-methyl-3H-imidazolium

Conditions
ConditionsYield
In water; acetonitrile Radiolysis;

174501-64-5Relevant articles and documents

High performance asymmetric supercapacitor based on MnO2 electrode in ionic liquid electrolyte

Zhang, Xuan,Zhao, Dandan,Zhao, Yongqing,Tang, Pengyi,Shen, Yinglin,Xu, Cailing,Li, Hulin,Xiao, Yu

, p. 3706 - 3712 (2013)

In this work, the electrochemical properties of a MnO2 nanocomposite electrode were investigated in 1-butyl-3-methyl-imidazolium hexafluorophosphate ([Bmim]PF6)/N,N-dimethylformamide (DMF) electrolyte. The [Bmim]PF6/DMF electrolyte with different volume fractions exhibits significant influence on the electrochemical properties of the electrode. When the volume ratio of [Bmim]PF6 and DMF was 1:1, the electrode showed the best electrochemical performance. The operation potential window of the MnO2 nanocomposite electrode in ionic liquids was 2.1 V and the specific capacitance according to the mass of MnO2 was 523.3 F g-1 at 3 A g-1. Then, a high-voltage (3 V) MnO2 asymmetric supercapacitor was successfully fabricated, using the MnO2 nanocomposite electrode, activated carbon and [Bmim]PF 6/DMF as the positive electrode, negative electrode and electrolyte, respectively. The MnO2 asymmetric supercapacitor displayed a maximum specific energy of 67.5 W h kg-1 at a specific power of 593.8 W kg-1 and a maximum specific power of 20.4 kW kg-1 at a specific energy of 8.5 W h kg-1. The impressive results showed that [Bmim]PF6/DMF could be a promising electrolyte for MnO2 supercapacitors.

One-pot and solventless synthesis of ionic liquids under ultrasonic irradiation

Estager, Julien,Lévêque, Jean-Marc,Cravotto, Giancarlo,Boffa, Luisa,Bonrath, Werner,Draye, Micheline

, p. 2065 - 2068 (2007)

A novel method is described for the one-pot synthesis of various ionic liquids in a competitive time. By using ultrasonic irradiation, different families of nitrogen-bearing ionic liquids can be obtained in a solvent-free or in aqueous medium, which gives a greener touch to the overall process. Georg Thieme Verlag Stuttgart.

Effect of temperature on the purity of product in the preparation of 1-butyl-3-methylimidazolium-based ionic liquids

K?rkk?inen, Johanna,Asikkala, Janne,Laitinen, Risto S.,Lajunen, Marja K.

, p. 763 - 770 (2004)

The preparation of room-temperature ionic liquids 1-butyl-3- methylimidazolium chloride, hexafluorophosphate, and dicyanamide by microwave-assisted reaction in non-solvent and solvent conditions has been studied in this contribution. A special emphasis is put on the effect of the reaction temperature on the purity of ionic liquids that was monitored by electrospray ionisation mass spectrometry and 1H NMR. The X-ray structure of 1-butyl-3-methylimidazolium chloride is presented.

Spectroscopic and photophysical properties of ZnTPP in a room temperature ionic liquid

Szmytkowski, Jedrzej,Bond, Toby,Paige, Matthew F.,Scott, Robert W. J.,Steer, Ronald P.

, p. 11471 - 11476 (2010)

The steady-state absorption and emission spectra and the time-resolved Soret- and Q-band excited fluorescence profiles of the model metalloporphyrin, ZnTPP, have been measured in a highly purified sample of the common room temperature ionic liquid, [bmim][PF6]. S2-S0 emission resulting from Soret-band excitation behaves in a manner completely consistent with that of molecular solvents of the same polarizability. The ionic nature of the solvent and its slow solvation relaxation times have no significant effect on the nature of the radiationless decay of the S2 state, which decays quantitatively to S1 at a population decay rate that is consistent with the weak coupling case of radiationless transition theory (energy gap law). The ratio of the intensities of the Qα:Qβ (0-0:1-0) bands is consistent with the solvatochromic shift correlation data obtained for molecular solvents. The temporal S1 fluorescence decay profiles measured at a single emission wavelength are biexponential; the longer-lived major component is similar to that observed for ZnTPP in molecular solvents, and the minor shorter-lived component is attributed to solvent relaxation processes on a nanosecond time scale.

Preparation of second generation ionic liquids by efficient solvent-free alkylation of N-heterocycles with chloroalkanes

Cravotto, Giancarlo,Gaudino, Emanuela Calcio,Boffa, Luisa,Leveque, Jean-Marc,Estager, Julien,Bonrath, Werner

, p. 149 - 156 (2008)

Non-conventional techniques, such as microwave (MW) and power ultrasound (US) as well as combined MW/US irradiation, have been used to promote one-pot synthesis of second-generation ionic liquids (ILs), cutting down reaction times and improving yields. However, the use of chloroalkanes in the alkylation of N-heterocycles requires more drastic conditions if results are to match those obtained with more reactive alkyl halides. The present paper describes a series of MW- or MW/US-promoted IL preparations starting from chloroalkanes and classic heterocycles (1-methylimidazole, pyridine and 1-methylpyrrolidine). When reactions were carried out under conventional heating in an oil bath they required longer reaction times and gave poorer yields. 1H-NMR analysis and ion-exchange chromatography showed that the present solventless procedure afforded ILs of satisfactory purity. The observed high yields (usually 70-98% isolated), and short reaction times showed that a straightforward access to ILs can be also achieved with the use of alkyl chlorides, resulting in a considerable reduction of costs.

Anthralin: Primary products of its redox reactions

Czerwinska, Malgorzata,Sikora, Adam,Szajerski, Piotr,Zielonka, Jacek,Adamus, Jan,Marcinek, Andrzej,Piech, Krzysztof,Bednarek, Pawel,Bally, Thomas

, p. 5312 - 5319 (2006)

One-electron reduction significantly enhances the ability of anthralin, 1, to act as a hydrogen atom donor. On annealing of an MTHF glass in which the radical anion of anthralin, 1.-, is generated radiolytically, this species decays mainly by loss of H. to give the anthralyl anion, 2. On the other hand, radicals formed on radiolysis of matrices that are suitable for the generation of radical anions or cations are capable to abstract H . from anthralin to give the anthralyl radical, 2.. Both 2- and 2. are obtained simultaneously by mesolytic cleavage of the radical anion of the anthralin dimer. Contrary to general assumptions, the anthralyl radical is found to be much more reactive toward oxygen than the anion. All intermediates are characterized spectroscopically and by reference to quantum chemical calculations. Attempts to generate the radical cation of anthralin by X-irradiation of an Ar matrix containing anthralin led also to significant formation of its radical anion, i.e., anthralin acts apparently as an efficient electron trap in such experiments.

Physicochemical properties and structures of room temperature ionic liquids. 1. Variation of anionic species

Tokuda, Hiroyuki,Hayamizu, Kikuko,Ishii, Kunikazu,Susan, Md. Abu Bin Hasan,Watanabe, Masayoshi

, p. 16593 - 16600 (2004)

Room-temperature ionic liquids (RTILs) based on 1-butyl-3-methylimidazolium ([bmim]) with a variety of fluorinated anions were prepared, and the thermal behavior, density, viscosity, self-diffusion coefficients of the cations and anions, and ionic conductivity were measured over a wide temperature range. The temperature dependencies of the self-diffusion coefficient, viscosity, ionic conductivity, and molar conductivity have been fitted to the Vogel-Fulcher-Tamman equation, and the best-fit parameters for the self-diffusion coefficient, viscosity, ionic conductivity, and molar conductivity have been estimated, together with the linear fitting parameters for the density. The self-diffusion coefficients determined for the individual ions by pulsed-field-gradient spin-echo NMR method exhibit higher values for the cation compared with the anion over a wide temperature range, even if its radius is larger than that of the anionic radii. The summation of the cationic and anionic diffusion coefficients for the RTILs follows the order [bmim][(CF3SO2N] > [bmim][CF 3CO2] > [bmim][CF3SO3] > [bmim][BF4] > [bmim][(C2F5SO 2)2N] > [bmim][PF6] at 30?°C, and the order of the diffusion coefficients greatly contrasts to the viscosity data. The ionic association is proposed from the results of the ratios of molar conductivity obtained from impedance measurements to that calculated by the ionic diffusivity using the Nernst-Einstein equation. The ratio for the ionic liquids follows the order [bmim][PF6] > [bmim][BF4] > [bmim][(C2F5SO2)2N] > [bmim][(CF3SO2)2N] > [bmim][CF 3SO3] > [bmim][CF3CO2] at 30?°C and provides quantitative information on the active ions contributing to ionic conduction in the diffusion components.

Liquid-Crystalline Ionic Liquids as Ordered Reaction Media for the Diels–Alder Reaction

Bruce, Duncan W.,Gao, Yanan,Canongia Lopes, José Nuno,Shimizu, Karina,Slattery, John M.

, p. 16113 - 16123 (2016)

Liquid-crystalline ionic liquids (LCILs) are ordered materials that have untapped potential to be used as reaction media for synthetic chemistry. This paper investigates the potential for the ordered structures of LCILs to influence the stereochemical outcome of the Diels–Alder reaction between cyclopentadiene and methyl acrylate. The ratio of endo- to exo-product from this reaction was monitored for a range of ionic liquids (ILs) and LCILs. Comparison of the endo:exo ratios in these reactions as a function of cation, anion and liquid crystallinity of the reaction media, allowed for the effects of liquid crystallinity to be distinguished from anion effects or cation alkyl chain length effects. These data strongly suggest that the proportion of exo-product increases as the reaction media is changed from an isotropic IL to a LCIL. A detailed molecular dynamics (MD) study suggests that this effect is related to different hydrogen bonding interactions between the reaction media and the exo- and endo-transition states in solvents with layered, smectic ordering compared to those that are isotropic.

Controlling the reactions of 1-bromogalactose acetate in methanol using ionic liquids as co-solvents

Gilbert, Alyssa,Haines, Ronald S.,Harper, Jason B.

, p. 5442 - 5452 (2020)

The reactions of an acetobromogalactose in mixtures of methanol and one of seven different ionic liquids with varying constituent ions were studied. In general, small amounts of ionic liquid in the reaction mixture led to increases in the rate constant compared to methanol, whilst large amounts of ionic liquid led to decreases in the rate constant; this outcome differs significantly from previous reactions proceeding through this mechansim. Temperature dependent kinetic studies indicated that the dominant interaction driving these changes was between the ionic liquid and the transition state of the process. Through considering solvent parameters of ionic liquids, a relationship was found between the changes in the rate constant and both the hydrogen bond accepting ability and polarisability of the solvent, indicating that the interactions affecting reaction outcome are both specific and non-specific in nature; once more, these interactions were different to those observed in previous similar reactions. By changing the amount of ionic liquid in the reaction mixture, additional products not seen in the molecular solvent case were observed, the ratios of which are dependent on the anion of the ionic liquid and the proportion of ionic liquid in the reaction mixture. This demonstrates the importance of considering solvent effects on both the rate and product determining steps and the potential application of such changes is discussed.

A general and direct synthesis of imidazolium ionic liquids using orthoesters

Kim, Do Joong,Oh, Kyung Hwan,Park, Jin Kyoon

, p. 4098 - 4101 (2014)

A general method to synthesize halide and halide-free ionic liquids was developed. Direct alkylation of imidazole and pyridine derivatives was performed in the presence of an acid using an orthoester as the alkyl donor yielding ionic liquid products. Residual Cl and water contents of the ionic liquids were determined by ion chromatography and a Karl-Fisher test. the Partner Organisations 2014.

How to predict the physical properties of ionic liquids: A volume-based approach

Slattery, John M.,Daguenet, Corinne,Dyson, Paul J.,Schubert, Thomas J. S.,Krossing, Ingo

, p. 5384 - 5388 (2007)

(Chemical Equation Presented) The molecular volume Vm (that is, the sum of the ionic volumes Vion of the constituent ions) of an ionic liquid (IL) in combination with an anion-dependent empirical relationship is all one needs to predict physical properties such as viscosity, conductivity, and density of [N(CN)2]-, [BF4]-, [PF6]-, and [N(SO2CF3) 2]- ionic liquids, including those which may as yet only exist on paper.

Ionic Liquids: Additives for Manipulating the Nucleophilicity

Rather, Mudasir Ahmad,Rather, Ghulam Mohammad,Pandit, Sarwar Ahmad,Bhat, Sajad Ahmad,Khan, Khaliquz Zaman,Bhat, Mohsin Ahmad

, p. 1518 - 1528 (2015)

Kinetic investigations of the SN2 reaction at the sulfur atom of p-toluenesulfonyl chloride with sodium azide in dried methanol in the presence of varying amounts of room temperature ionic liquids (RTILs), 1-butyl-3-methylimidazolium acetate ([C4C1im][CH3COO]), 1-butyl-3-methylimidazolium chloride ([C4C1im]Cl) and 1-butyl-3-methylimidazolium hexafluorophosphate ([C4C1im][PF6]), were carried out in order to explore and understand the impact of these additives on the rate of such reactions. The observed results indicate that the rate constant of the reaction increase appreciably with increases in the concentration of RTILs in RTIL-methanol binary solvent systems. The results were analyzed in light of a Kamlet-Taft model system, which established that the observed impact of RTILs can be attributed to the cumulative effects of increase in the β value (hydrogen bonding acceptor ability) which is expected to enhance the reactivity of p-toluenesulfonyl chloride as well as the nucleophilicity of the azide ion and decrease in the πvalue (solvent dipolarity/polarizability) which is expected to enhance the reactivity of the azide ion. Of the three ionic liquids used in the presented studies, [C4C1im][CH3COO] was observed to be more effective in accelerating the rate constant; this we attribute to its comparatively stronger ability to increase the β value and decrease the πvalue in the mixed solvent system.

Introduction of an ordered porous polymer network into a ceramic alumina membrane via non-hydrolytic sol-gel methodology for targeted dynamic separation

Meng, Minjia,Liu, Yan,Zhang, Min,Feng, Yonghai,Yan, Yongsheng

, p. 38630 - 38642 (2014)

A highly selective composite imprinted alumina membrane (CIAM) for gentisic acid (GA) was successfully synthesized by the nonhydrolytic sol-gel (NHSG) method with room temperature ionic liquid (RTIL) as the pore template. The carboxylic acid was used as both the functional monomer and the catalyst to form the alumina membrane-based porous imprinted polymer layer. The adsorption capacities, fluxes and permeation selectivities of various CIAMs suggested that cinnamic acid (CA) was the promising functional monomer for preparing a CIAM to separate GA from salicylic acid (SA) and the incorporation of RTIL improved the selectivity of GA over CIAM. The amount of porous imprinted polymer layer on the CIAM significantly affected the separation of GA from SA over CIAM. A three-level Box-Behnken experimental design with three factors combining the response surface modeling was used to optimize the dynamic separation process. The experimental data were well fitted to a second-order polynomial equation using multiple regression analysis. The optimal conditions for the separation of GA from SA were as follows: GA concentration of 0.0325 mmol L-1, temperature of 15.0 °C and flow rate of 1.0 mL min-1. Under these conditions, the experimental separation factor was 13.26 ± 0.87%, which was close to the predicted separation factor. the Partner Organisations 2014.

Separation/preconcentration of trace copper by extraction into [C 4mim] [PF6] RITL containing p-tert-butyl-calix[4]arene functionalized with o-phenanthroline prior to flame absorption atomic spectrometry

Ma, Lina,Zhu, Xiashi,Wang, Wenjun

, p. 20 - 24 (2013)

A liquid-liquid extraction (LLE)-flame atomic absorption spectrometry (FAAS) for the separation/analysis of copper has been developed. The method was based on the fact that the inclusion complex of copper(II) with 25, 27-di (5-phenanthrolinylaminocarbonylmethoxy)-26,28-dihydroxy-p-tert-butylcalix[4] arene (TBCP) could be extracted into room temperature ionic liquids (RTILs, 1-butyl-3-methylimidazolium hexafluoro-phosphate [C4mim] [PF 6] as the green extractant, TBCP as the complexlant), and the copper(II) was subsequently determined by FAAS. The LLE was optimized in detail. The selectivity and mechanism of LLE were approached. Under optimized experimental conditions, the linear range of calibration curve for the determination of copper(II) was 0.020-10.0 μg/mL. The detection limit estimated (S/N = 3) was 3.59 ng/mL with 3.0% RSD. It has been applied for the determination of copper(II) in water samples with satisfactory results.

Impregnation of different ionic liquids onto cationic starch and their comparison in the extraction of Th(IV)

Bursali, Elif Ant,Bozkurt, Serap Seyhan,Yurdako?, Mürüvvet

, p. 364 - 372 (2016)

Cationic starch (CS) was prepared by using epichlorohydrin (EPI) and 3-chloro-2-hydroxypropyltrimethylammonium chloride (CHPTMA) and ionic liquids (ILs) having different anionic groups [1-butyl-3-methyl imidazolium tetrafluoroborate (BMI+ BF-4), ),lyhtem-3-lytub-1imidazolium (BMIIMB(+ Br Br-), 1-butyl-3-methyl imidazolium hexafluorophosphate (BMI+ PF-6 ), and 1-butyl-3-methyl imidazolium bis-[(trifluoromethyl)sulfonyl]imide (BMI+ [(TF)2 N]-)] were impregnated onto CS. Thorium(IV) ions were preconcentrated by using IL impregnated CS. The effects of ILs were investigated for extraction of Th(IV) by CS and the results were compared. Th(IV) was preconcentrated with approximately 73% sorption capacity by CS and increased up to 98%-100% for IL impregnated sorbents at pH 7.0. The sorption capacities of Th(IV) were 0.453 mmol g-1 , 0.399 mmol g-1 , 0.281 mmol g-1 , and 0.183 mmol g-1 CS-BMI+ Br- , CS-BMI+ [(TF)2 N], CS-BMI+ PF-6 andCS-BMI+ BF-4 , respectively. The elution occurred with HCl and NaOH solutions at pH 7.0. for.

Do anions influence the polarity of protic ionic liquids?

Shukla, Shashi Kant,Khupse, Nageshwar D.,Kumar, Anil

, p. 2754 - 2761 (2012)

Polarity studies in two classes of imidazolium-based protic ionic liquids (PILs) possessing [HSO4]-, [HCOO]-, [CH 3COO]- and [CH3CH2COO]- anions were carried out using a solvatochromic method from 298.15 to 353.15 K. For 1-methylimidazolium class of PILs, ET(30) was found to be independent over the entire range of temperature, while ET(30) was noted to decrease with a rise in temperature in the case of 1-butylimidazolium class of PILs containing [CH3COO]- and [CH 3CH2COO]- anions. The ET(30) value decreases in both the classes upon varying the anions ([HSO4] -, [HCOO]-, [CH3COO]- and [CH 3CH2COO]-). The ET(30) value is controlled by hydrogen bond acceptor basicity, β, and dipolarity/ polarizability, π*. The ET(30) value for PILs varies inversely to the strength of the coulombic interaction between ions in PILs. Strong interactions between ions lead to lower ET(30) values. Unlike the poor thermal effect on ET(30), the Kamlet-Taft parameters i.e. α, β and π* have pronounced thermal effect in the imidazolium-based PILs. Variation in the Kamlet-Taft parameters is controlled by the stabilization of ions and the degree of proton transfer from Bronsted acid to Bronsted base. the Owner Societies 2012.

Simultaneous determination of Brilliant Green and Crystal Violet dyes in fish and water samples with dispersive liquid-liquid micro-extraction using ionic liquid followed by zero crossing first derivative spectrophotometric analysis method

Sadeghi, Susan,Nasehi, Zohreh

, p. 134 - 142 (2018)

In this study, dispersive liquid-liquid micro-extraction using ionic liquid (IL-DLLME) combined with zero crossing first derivative spectrophotometric method was applied to quantitative determination of triphenylmethane dyes in binary mixtures. The 1-methyl-3-octylimidazolium hexafluorophosphate [OMIM][PF6] ionic liquid was used to extract Brilliant Green (BG) and Crystal Violet(CV) dyes from aqueous solutions. The amplitude of the zero crossing first derivative spectra at 670 nm and 532 nm were selected for the determination of BG and CV, respectively. Significant factors influencing the extraction of BG and CV such as sample pH, kind of extraction solvent, amount of extractant, extraction and centrifuging times and ionic strength were investigated. Under the optimal conditions, the calibration curves for the simultaneous determination of both dyes were found to be linear in the range of 10–500 μg L?1 with detection limits (LODs) of 2.7 μg L?1 and 1.4 μg L?1 for BG and CV, respectively. The relative standard deviation (RSD%) for five replicate simultaneous determinations of BG and CV were 4.7% and 1.7%, respectively. Extraction efficiencies of the BG and CV dyes in the presence of interfering ions were also investigated. Sample preparation based on the quick, easy, cheap, effective, rugged and safe (QuEChERS) extraction combined with the IL-DLLME method and zero crossing first derivative spectrophotometric detection was applied for the simultaneous analysis of BG and CV in fish and water samples with quantitative recoveries.

Correlating ionic liquid solvent effects with solvent parameters for a reaction that proceeds through a xanthylium intermediate

Gilbert, Alyssa,Bucher, G?tz,Haines, Ronald S.,Harper, Jason B.

, p. 9336 - 9342 (2019)

A unimolecular nucleophilic substitution reaction that proceeds through a xanthylium carbocation was studied in seven ionic liquid solvents. It was found that the general trend in the rate constant with changing proportion of ionic liquid in the reaction mixture was different to that seen for other unimolecular processes, with the rate constant increasing as more ionic liquid was added to the reaction mixture. A significant correlation was found between the natural logarithm of the rate constant and a combination of the Kamlet-Taft solvent parameters. This relationship indicated that the principal interaction involved hydrogen bonding between the ionic liquid and some species along the reaction coordinate. Further, this correlation enables prediction of the effects that other ionic liquids will have on this, and other, reactions that proceed through a similar intermediate.

Interactions of 1-butyl-3-methylimidazolium hexafluorophosphate with N,N-dimethylformamide: Density and viscosity measurements

Bennett,Dikio,Angaye,Wankasi,Dikio,Bahadur,Ebenso

, p. 661 - 666 (2016)

Physico-chemical properties: density (ρ) and viscosity (η) at (303.15, 313.15 and 323.15) K were measured for the binary mixtures of synthesized and characterized ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate [BMIM][PF6] with N,N

Solvent-solute interactions in ionic liquids

Crowhurst, Lorna,Mawdsley, Philip R.,Perez-Arlandis, Juan M.,Salter, Paul A.,Welton, Tom

, p. 2790 - 2794 (2003)

A range of ionic liquids was studied utilizing the Kamlet-Taft parameters hydrogen bond acidity (α), hydrogen bond basicity (β), and dipolarity/polarizability effects (π*). Some of the ionic liquids studied were methanol, acetonitrile, acetone, dichloromethane, toluene, hexane, and water. π* was high for all the ionic liquids investigated and varied with both anion and cation. α was generally moderate and depended chiefly on the cation. β was also moderate and depended mainly on the anion. Comparison was made with other polarity measurements in ionic liquids.

Dynamic solvation in room-temperature ionic liquids

Chowdhury,Halder,Sanders,Calhoun,Anderson,Armstrong,Song,Petrich

, p. 10245 - 10255 (2004)

The dynamic solvation of the fluorescent probe, coumarin 153, is measured in five room-temperature ionic liquids using different experimental techniques and methods of data analysis. With time-resolved stimulated-emission and time-correlated single-photon counting techniques, it is found that the solvation is comprised of an initial rapid component of a??55 ps. In all the solvents, half or more of the solvation is completed within 100 ps. The remainder of the solvation occurs on a much longer time scale. The emission spectra of coumarin 153 are nearly superimposable at all temperatures in a given solvent unless they are obtained using the supercooled liquid, suggesting that the solvents have an essentially glassy nature. The physical origin of the two components is discussed in terms of the polarizability of the organic cation for the faster one and the relative diffusional motion of the cations and the anions for the slower one. A comparison of the solvation response functions obtained from single-wavelength and from spectral-reconstruction measurements is provided. Preliminary fluorescence-upconversion measurements are presented against which the appropriateness of the single-wavelength method for constructing solvation correlation functions and the use of stimulated-emission measurements is considered. These measurements are consistent with the trends mentioned above, but a comparison indicates that the presence of one or more excited states distorts the stimulated-emission kinetics such that they do not perfectly reproduce the spontaneous emission data. Fluorescence-upconversion results indicate an initial solvation component on the order of a??7 ps.

Synthesis and physical-chemical properties of ionic liquids based on 1- n-butyl-3-methylimidazolium cation

Suarez,Einloft,Dullius,De Souza,Dupont

, p. 1626 - 1639 (1998)

The reaction of 1-n-butyl-3-methylimidazolium chloride (BMI.Cl) with sodium tetrafluoroborate or sodium hexafluorophosphate affords the molten salts BMI.X (1, X = BF4 and 2, X = PF6). Compounds 1 and 2 are viscous liquids within a wide range of temperature (down to 192 K). IR, NMR, density, viscosity and conductivity measurements suggest that compound 2 behaves quasi-molecular. Compound 1 is quasi-molecular below 279 K, but at higher temperatures is probably composed of imidazolium and tetrafluoroborate ions in an extended hydrogen-bonded network.

Biosynthesis of glycyrrhetic acid 3-O-mono-β-d-glucuronide catalyzed by β-d-glucuronidase with enhanced bond selectivity in an ionic liquid/buffer biphasic system

He, Dong-Mei,Kaleem, Imdad,Qin, Si-Ying,Dai, Da-Zhang,Liu, Gui-Yan,Li, Chun

, p. 1916 - 1922 (2010)

The bond selective hydrolysis of glycyrrhizin (GL) to glycyrrhetic acid 3-O-mono-β-d-glucuronide (GAMG) catalyzed by recombinant β-d-glucuronidase from Escherichia coli BL21 (PGUS-E) was successfully performed in an ionic liquid (IL)/buffer biphasic system. Five ILs were analyzed, however, a hydrophobic IL 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIM]PF6) showed the best biocompatibility with PGUS-E. An obvious enhancement in the initial reaction rate, substrate conversion, GAMG yield and chemical bond selectivity (Scb) was observed using 40% (v/v) [BMIM]PF6/buffer as the reaction medium when compared to the acetate buffer medium. Under the optimized conditions (pH 6.0, temperature 50°C, substrate concentration 6mM and shaking speed 200rpm), the initial reaction rate, the GAMG yield and the Scb reached 3.15mMh-1, 74.36% and 98.12%, respectively. The recyclability of [BMIM]PF6 was also studied and found to be reusable for five batches with high recovery percentage (≥92%). Furthermore, the desired product and byproduct were easily separated since they were distributed in different phases. Additionally, higher Vmax (3.14 versus 2.24mMh-1), lower apparent Km (1.21 versus 1.80mM) and Ea (25.97 versus 32.60kJmol-1) were achieved in [BMIM]PF6/buffer biphasic system than that in monophasic buffer system.

Convenient synthesis of various ionic liquids from onium hydroxides and ammonium salts

Peng, Yanqing,Li, Guiyun,Li, Jianguo,Yu, Shaojun

, p. 4286 - 4288 (2009)

Hydroxide ionic liquids, such as 1-alkyl-3-methylimidazolium hydroxides, undergo smooth anion metathesis with ammonium salts to produce a variety of ionic liquids in excellent yields. It is a practical supplement of traditional neutralization method due to the broader range of starting materials containing desired anions.

Probing the importance of ionic liquid structure: A general ionic liquid effect on an SNAr process

Tanner, Eden E. L.,Hawker, Rebecca R.,Yau, Hon Man,Croft, Anna K.,Harper, Jason B.

, p. 7516 - 7521 (2013)

The effect of a range of ionic liquids, with systematic variations in the cation and anion, on the rate constant of an aromatic substitution process was investigated. Temperature-dependent kinetic data allowed calculation of activation parameters for the process in each solvent. These data demonstrate a generalised ionic liquid effect, with an increase in rate constant observed in each ionic solvent, though the microscopic origins of the rate constant enhancement differ with the nature of the ionic liquid.

β-Diimine-methallyl nickel complexes in ionic liquid: A biphasic green system for the high selective styrene dimerization

Landolsi, Kamel,Msaddek, Moncef

, (2022/02/23)

The selective head-to-tail dimerization of styrene to 1,3-diphenyl-1-butene over [Ni(β-diimine)- (methallyl)]+PF6- / Et2O?HBF4 catalyst system has been investigated. The styrene conversion up to 95 % and the TOF (TOF = 508 h?1) were reached after optimization of the reaction parameters (temperature: T = 80 °C; time: t = 1 h…) with selectivity to E-1,3-diphényl-1-butene stereoisomer up to 98%. Solvents and diimine ligands have a strong effect on the catalyst activity. The substituents on the β-diimine ligands have a crucial effect on the conversion but did not affect the selectivity. Cationic β-diimine-nickel (2 + ) is the likely active species. Reaction products were characterized by 1H and 13C NMR, IR, and GC–MS spectroscopies.

Red Propolis as a Source of Antimicrobial Phytochemicals: Extraction Using High-Performance Alternative Solvents

dos Santos, Cíntia M.,de Souza Mesquita, Leonardo M.,Braga, Anna Rafaela C.,de Rosso, Veridiana V.

, (2021/06/28)

Propolis is a resinous material rich in flavonoids and involved in several biological activities such as antimicrobial, fungicide, and antiparasitic functions. Conventionally, ethanolic solutions are used to obtain propolis phytochemicals, which restrict their use in some cultures. Given this, we developed an alcohol-free high-performance extractive approach to recover antibacterial and antioxidants phytochemicals from red propolis. Thus, aqueous-solutions of ionic liquids (IL) and eutectic solvents were used and then tested for their total flavonoids, antioxidant, and antimicrobial activities. The surface-responsive technique was applied regarding some variables, namely, the time of extraction, the number of extractions, and cavitation power (W), to optimize the process (in terms of higher yields of flavonoids and better antioxidant activity). After that, four extractions with the same biomass (repetitions) using 1-hexyl-3-methylimidazolium chloride [C6mim]Cl, under the operational conditions fixed at 3.3 min and 300 W, were able to recover 394.39 ± 36.30 mg RuE. g?1 of total flavonoids, with total antioxidant capacity evaluated up to 7595.77 ± 5.48 μmol TE. g?1dried biomass, besides inhibiting the growth of Staphylococcus aureus and Salmonella enteritidis bacteria (inhibition halo of 23.0 ± 1.0 and 15.7 ± 2.1, respectively). Aiming at the development of new technologies, the antimicrobial effect also presented by [C6mim]Cl may be appealing, and future studies are required to understand possible synergistic actions with propolis phytochemicals. Thereby, we successfully applied a completely alcohol-free method to obtain antimicrobials phytochemicals and highly antioxidants from red propolis, representing an optimized process to replace the conventional extracts produced until now.

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