Epichlorohydrin → HCID 54125222, compound

HRID 1730841Notes

Reaction equation

HRID 1730841 reaction equation
[CH2:1]([O:3][O:4][P:5]([CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[NH:15][C:14]1=[O:21])([O:7][O:8][CH2:9][CH3:10])=[O:6])[CH3:2].[CH2:22]([CH:24]1[O:26][CH2:25]1)Cl.[OH-].[Na+]>[Cl-].C[N+](C)(C)C>[CH2:22]([N:15]1[C:16]([CH3:19])([CH3:20])[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:21])[CH:24]1[O:26][CH2:25]1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 54162008HCID 54162008, compound

Product 1

HCID 54125222HCID 54125222, compound

Reagents, catalysts & solvents 1

HCID 6379Tetramethylammonium chlorideCatalyst

Conditions

Temperature
105 °C

Procedure

A mixture of 146.1 g of 3-(diethoxyphosphonoethyl)-5,5-dimethyl-hydantoin (0.5 mol), 694 g of epichlorohydrin (7.5 mols) and 0.5 g of tetramethylammonium chloride is stirred for 105 minutes at 105° C. 44 g of 50% strength aqueous sodium hydroxide solution are added dropwise over the course of 3 hours at 60° C, analogously to Example 1 (c). The mixture is worked up analogously to Example 1 (c) and 157 g of a yellow, clear resin (90.2% of theory) with 2.74 epoxide equivalents/kg (95.5% of theory) and a phosphorus content of 6.13% are obtained.

Sources & evidence

ORD record
ord-c1e5dff91bf2436b9ab9c5c225f64237
Source dataset
uspto-grants-1976_11
Patent number
US03994858

Reaction notes

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