2-(Dibutylamino)ethanol → N,N-dibutylethanolamine triethylene glycol monobutyl ether borate

HRID 1840689Notes

Reaction equation

HRID 1840689 reaction equation
[B:1]([OH:4])([OH:3])[OH:2].[CH2:5]([O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17]O)[CH2:6][CH2:7][CH3:8].[CH2:19]([N:23]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:24][CH2:25][OH:26])[CH2:20][CH2:21][CH3:22]>C1(C)C=CC=CC=1>[CH2:19]([N:23]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:24][CH2:25][OH:26])[CH2:20][CH2:21][CH3:22].[B:1]([O-:4])([O-:3])[O:2][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 76212-(Dibutylamino)ethanolHCID 7628Boric AcidHCID 8923Triethylene glycol monobutyl ether

Product 1

HCID 86588641N,N-dibutylethanolamine triethylene glycol monobutyl ether borateYield 128.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N,N-dibutylethanolamine/triethylene glycol monobutyl ether borate was prepared as follows. Boric acid (10.3 grams), triethylene glycol monobutyl ether (Fluka, 64.1 grams), and N,N-dibutylethanolamine (28.9 grams) were added to a 250 milliliter flask. One hundred fifty milliliters of toluene was then added. The reaction was allowed to proceed overnight at 110° C., and the byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation. The final solution was evaporated to remove toluene under vacuum, and a brownish liquid product (˜90 grams) of N,N-dibutylethanolamine/triethylene glycol monobutyl ether borate was obtained.

Workup

  1. customN,N-dibutylethanolamine/triethylene glycol monobutyl ether borate was prepared
  2. customthe byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation
  3. customThe final solution was evaporated
  4. customto remove toluene under vacuum

Sources & evidence

ORD record
ord-5d0f452b2bdc4522921bee4d29b21ecf
Source dataset
uspto-grants-2004_01
Patent number
US06682591B2

Reaction notes

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