Carbon Dioxide → Tributylphosphine

HRID 329830Notes

Reaction equation

HRID 329830 reaction equation
C(=O)([O-])[O-].[CH2:5]([P+:9]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:11][CH2:12][CH2:13][CH3:14])[CH3:10])[CH2:6][CH2:7][CH3:8].[CH2:19]([P+:23]([CH3:32])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH3:22].[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37].C(=O)=O>O>[CH2:15]([P:9]([CH2:5][CH2:6][CH2:7][CH3:8])[CH2:11][CH2:12][CH2:13][CH3:14])[CH2:16][CH2:17][CH3:18].[C:33]([O-:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([O-:38])=[O:37].[CH2:28]([P+:23]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:24][CH2:25][CH2:26][CH3:27])[CH3:32])[CH2:29][CH2:30][CH3:31].[CH2:5]([P+:9]([CH3:10])([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:15][CH2:16][CH2:17][CH3:18])[CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 444266Maleic AcidHCID 86743661HCID 86743661, compound

Product 2

HCID 13831TributylphosphineHCID 86743660HCID 86743660, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In 10.0 g of water was dissolved 10.0 g of tri-n-butylmethylphosphonium carbonate obtained as in Example 12 (1st step) and a solution of 4.2 g of maleic acid dissolved in 5.0 g of water was gradually added to the solution, whereby carbon dioxide simultaneously generated vigorously. For more completely removing carbon dioxide, degassing was performed for 2 hours at 40° C. and 20 mmHg and after confirming carbonate ions being less than 2 ppm, water was distilled off. The residue formed was recrystallized from methyl ethyl ketone to produce 1-1.2 g (94.1% of the theoretical yield, yield of 59.8% to tri-n-butylphosphine) of tri-n-butylmethylphosphonium monomaleate.

Workup

  1. customobtained as in Example 12 (1st step)
  2. customFor more completely removing carbon dioxide, degassing
  3. distillationwas distilled off
  4. customThe residue formed
  5. customwas recrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-5ab61bab052f4c1da1c1530b5098c1ce
Source dataset
uspto-grants-1990_01
Patent number
US04892944

Reaction notes

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