Epichlorohydrin → HCID 66723969, compound

HRID 2382519Notes

Reaction equation

[CH2:1]([CH:3]1[O:5][CH2:4]1)[Cl:2].[O:6]([C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)C>[O:6]([C:13]1[CH:14]=[CH:15][C:16]([N:17]([CH2:4][CH:3]([OH:5])[CH2:1][Cl:2])[CH2:4][CH:3]([OH:5])[CH2:1][Cl:2])=[CH:18][CH:19]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 70 °C

Procedure

In a four-necked flask equipped with a thermometer, dropping funnel, cooling pipe and stirrer, 610.6 g (6.6 mol) of epichlorohydrin was poured and heated up to a temperature of 70° C. while performing nitrogen purge, and a solution of 203.7 g (1.1 mol) of p-phenoxy aniline dissolved in 1,020 g of ethanol was dropped in 4 hours. The solution is stirred for additional 6 hours to ensure completion of the addition reaction to provide 4-phenoxy-N,N-bis(2-hydroxy-3-chloropropyl)aniline. Then, the flask was heated up to an internal temperature of 25° C., and 229 g (2.75 mol) of 48% aqueous NaOH solution was dropped in 2 hours, followed by additional stirring for 1 hour. After the completion of the cyclization reaction, ethanol was evaporated and extraction was carried out with 408 g of toluene, followed by washing twice with 5% saline solution. Toluene and epichlorohydrin were removed from the organic layer under reduced pressure, resulting in 308.5 g (yield 94.5%) of a brown viscous liquid. The main product N,N-diglycidyl-4-phenoxy aniline had a purity of 91% (GC area %).

Workup

customIn a four-necked flask equipped with a thermometer
additionwas poured
custompurge
additionwas dropped in 4 hours
additioncompletion of the addition reaction

Sources & evidence

ORD record: ord-7f9e8759e189437682d5d769de7f965a
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263216B2

Reaction notes

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