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Water → 1,2,3,4-Tetramethylimidazolinium dibutyl phosphate

HRID 72068
Notes
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Reaction equation

HRID 72068 reaction equation
[P:1]([O:13]CCCC)([O:8][CH2:9][CH2:10][CH2:11][CH3:12])([O:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:2].COC(=O)[O-].[CH3:23][NH+:24]1[CH2:28][CH:27]([CH3:29])[N:26]([CH3:30])[CH:25]1[CH3:31].O>CO>[CH2:9]([O:8][P:1]([O-:13])([O:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:2])[CH2:10][CH2:11][CH3:12].[CH3:23][NH+:24]1[CH2:28][CH:27]([CH3:29])[N:26]([CH3:30])[CH:25]1[CH3:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 31357Tributyl Phosphate2×HCID 675213621,2,3,4-Tetramethylimidazolinium methyl carbonate

Product 1

HCID 675214031,2,3,4-Tetramethylimidazolinium dibutyl phosphate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
100 °C

Procedure

By adding 62 parts of tributyl phosphate to the above-described methanol solution of 46 parts of 1,2,3,4-tetramethylimidazolinium methylcarbonate salt, followed by addition of 5.4 parts of water and stirring at 100° C. for 20 hours, tributyl phosphate was hydrolyzed and a salt exchange reaction was carried out to obtain a methanol solution of 1,2,3,4-tetramethylimidazolinium dibutyl phosphate monoanion. The above-described solution was heated under reduced pressure of 1.0 kPa or less at 50° C. to distill methanol until no distillate of methanol was observed. Thereafter, the temperature was raised from 50° C. to 100° C. and heating was continued for 30 minutes to distill and remove monomethyl carbonate (HOCO2CH3), methanol, and carbon dioxide (slight amounts of methanol and carbon dioxide are formed by thermal decomposition of monomethyl carbonate. Hereinafter, these are abbreviated as by-products). Thus, 1,2,3,4-tetramethylimidazolinium dibutyl phosphate monoanion, electrolyte (C-1), was obtained. The yield was 99 parts (yield based on the weight of 46 parts of 1,2,3,4-tetramethylimidazolinium methyl carbonate salt; hereinafter the same shall apply). The molecular weight of the electrolyte (C-1) was 280.

Workup

  1. customa salt exchange reaction

Sources & evidence

ORD record
ord-d90a335ed188489796c079b0d056015e
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08828261B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes