Phthalic Acid → Phthalate;bis(1,2,3,4-tetramethylimidazolidin-1-ium)

HRID 72071

Reaction equation

HRID 72071 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([OH:6])=[O:5].COC(=O)[O-].[CH3:18][NH+:19]1[CH2:23][CH:22]([CH3:24])[N:21]([CH3:25])[CH:20]1[CH3:26]>CO>[C:1]([O-:12])(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([O-:6])=[O:5].[CH3:18][NH+:19]1[CH2:23][CH:22]([CH3:24])[N:21]([CH3:25])[CH:20]1[CH3:26].[CH3:18][NH+:19]1[CH2:23][CH:22]([CH3:24])[N:21]([CH3:25])[CH:20]1[CH3:26]

Participants

4

Reactant 2

HCID 1017Phthalic AcidHCID 675213621,2,3,4-Tetramethylimidazolinium methyl carbonate

Product 1

HCID 66847151Phthalate;bis(1,2,3,4-tetramethylimidazolidin-1-ium)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

By adding 42 parts of phthalic acid (produced by Kawasaki Kasei Chemicals, Ltd.) to the methanol solution of 46 parts of 1,2,3,4-tetramethylimidazolinium methyl carbonate salt obtained in Production Example 1 and carrying out a salt exchange reaction, there was obtained a methanol solution of 1,2,3,4-tetramethylimidazolinium phthalate 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 phthalate monoanion (N-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 (N-1) was 280.

Workup

  1. customobtained in Production Example 1
  2. customa salt exchange reaction

Sources & evidence

ORD record
ord-de787e3bcda74d6eaf6eb8ae4f6f3ca4
Source dataset
uspto-grants-2014_09
Patent number
US08828261B2

Linked notes

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