Diethanolamine → 2,2',2'',2'''-(Hexane-1,6-diyldinitrilo)tetra(ethan-1-ol)

Temperature

57.5 °C

N,N-Diethanolamine (1331.3 g, 11.36 mol) is placed in a 5000 ml three-necked round bottomed flask fitted with a condenser, addition funnel, internal thermometer, mechanical stirrer and argon inlet. 1,6-Dibromohexane (1386 g, 5.68 mol) is added via the addition funnel slowly to keep the reaction temperature below 60° C. After addition is completed the mixture is heated to 55-60° C. for 18 h. The reaction mixture is poured into a 6 L Erlenmeyer flask containing a solution of methanol (1.5 L) and sodium hydroxide (227.2 g, 5.68 mol). White salts begin to precipitate. After 4 h, the mixture is filtered. The filtrate is concentrated under reduced pressure to leave the product as a viscous oil.

1. customfitted with a condenser, addition funnel
2. customthe reaction temperature below 60° C
3. additionAfter addition
4. additionThe reaction mixture is poured into a 6 L Erlenmeyer flask
5. customto precipitate
6. filtrationthe mixture is filtered
7. concentrationThe filtrate is concentrated under reduced pressure

ORD record

ord-0c32e3622a20475282538655b81ea390

Source dataset

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06211140B1