Epichlorohydrin → HCID 54361493, compound

HRID 1730840Notes

Reaction equation

HRID 1730840 reaction equation
[CH2:1]([O:3][O:4][P:5]([CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]([CH2:20][CH3:21])([CH3:19])[NH:15][C:14]1=[O:22])([O:7][O:8][CH2:9][CH3:10])=[O:6])[CH3:2].[CH2:23]([CH:25]1[O:27][CH2:26]1)Cl.[OH-].[Na+].ClCl.[P]>[Cl-].C[N+](C)(C)C.O>[CH2:23]([N:15]1[C:16]([CH2:20][CH3:21])([CH3:19])[C:17](=[O:18])[N:13]([CH2:12][CH2:11][P:5]([O:7][O:8][CH2:9][CH3:10])([O:4][O:3][CH2:1][CH3:2])=[O:6])[C:14]1=[O:22])[CH:25]1[O:27][CH2:26]1

Participants

8

Reactant 5

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 24526ChlorineHCID 5462309PhosphorusHCID 54456247HCID 54456247, compound

Product 1

HCID 54361493HCID 54361493, compound

Reagents, catalysts & solvents 2

HCID 6379Tetramethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

61.2 g of 3-(diethoxyphosphonoethyl)-5-ethyl-5-methyl-hydantoin (0.2 mol), 277.5 g of epichlorohydrin (3.0 mols) and 0.2 g of tetramethylammonium chloride are stirred for 90 minutes at 115° - 119° C. The mixture is then cooled to 60° C and 17.6 g of 50% strength aqueous sodium hydroxide solution are added dropwise over the course of 4 hours whilst stirring, under a waterpump vacuum. The water present in the mixture is removed by azeotropic circulatory distillation analogously to Example 1 (c). The mixture is worked up analogously to Example 1 (c) and 65.7 g of a yellow, clear, viscous resin (90.6% of theory) having an epoxide content of 2.71 epoxide equivalents/kg (96.7% of theory) are obtained. The product contains 0.65% of chlorine and 6.72% of phosphorus.

Workup

  1. customare obtained

Sources & evidence

ORD record
ord-fbffff432aba4c9a8fc9fd94c1061d2e
Source dataset
uspto-grants-1976_11
Patent number
US03994858

Reaction notes

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