Glycerol → HCID 19019648, compound

HRID 1109783Notes

Reaction equation

HRID 1109783 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[OH:12][CH2:13][CH:14]([CH2:16][OH:17])[OH:15].[CH2:18]([CH:20]1[O:22][CH2:21]1)Cl.[OH-:23].[Na+].ClCl>C(C(C)=O)C(C)C.[Cl-].C[N+](C)(C)C>[C:21]([O:12][CH2:13][CH:14]([CH2:16][O:17][C:4](=[O:5])[C:3]1[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:1]([OH:6])=[O:11])[OH:15])(=[O:22])[C:20]1[C:3](=[CH:2][CH:10]=[CH:9][CH:18]=1)[C:4]([OH:5])=[O:23]

Participants

8

Reactant 5

HCID 753GlycerolHCID 6811Phthalic AnhydrideHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 24526Chlorine

Product 1

HCID 19019648HCID 19019648, compound

Reagents, catalysts & solvents 2

HCID 6379Tetramethylammonium chlorideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

The reaction is carried out substantially as described in Example 5, initially giving 1165 g (100% of theory) of the desired hemiester as a pale yellow solid with an acid value of 5.27 equivalents/kg from the reaction of 888.7 g (6 mol) of phthalic anhydride and 276.3 g (3 mol) of glycerol in 960 g of methyl isobutyl ketone. Then 450 g (2.37 equivalents) of this hemiester are reacted using 2193 g (23.7 mol) of epichlorohydrin, 208.6 g of a 50% aqueous solution of sodium hydroxide and two times 21 g of a 50% aqueous solution of tetramethylammonium chloride, to give 509.4 g (86% of theory) of the desired yellow viscous product having an epoxy value of 3.38 equivalents/kg (85% of theory) and a chlorine content of 1.4%.

Workup

  1. custominitially giving 1165 g (100% of theory) of the desired hemiester as a pale yellow solid with an acid value of 5.27 equivalents/kg
  2. customThen 450 g (2.37 equivalents) of this hemiester are reacted
  3. customto give 509.4 g (86% of theory) of the desired yellow viscous product

Sources & evidence

ORD record
ord-22a0db16b32b439abbf46ceb1834e1d7
Source dataset
uspto-grants-1994_06
Patent number
US05322907

Reaction notes

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