Water → Diisopropanolamine

HRID 1278447Notes

Reaction equation

HRID 1278447 reaction equation
[OH-].[Na+].O.[CH3:4][CH:5]1[O:9][C:8](=[O:10])[N:7]([CH2:11][CH:12]([OH:14])[CH3:13])[CH2:6]1>>[CH3:4][CH:5]1[O:9][C:8](=[O:10])[N:7]([CH2:11][CH:12]([OH:14])[CH3:13])[CH2:6]1.[CH3:4][CH:5]([OH:9])[CH2:6][NH:7][CH2:11][CH:12]([OH:14])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 188023-(2-Hydroxypropyl)-5-methyl-2-oxazolidinone

Product 2

HCID 8086DiisopropanolamineHCID 188023-(2-Hydroxypropyl)-5-methyl-2-oxazolidinone

Conditions

Temperature
95 °C

Procedure

When 0.224 mol of NaOH in 1.11 mole of water was mixed with 1 mol of 5-methyl-N-(2-hydroxypropyl) oxazolidin-2-one (MHPO) and the mixture heated at 95° C. for five hours there was obtained about a 13 percent conversion of the MHPO to diisopropanolamine (DIPA). After 29 hours at 95° C. only 13.9% conversion was achieved. Following the addition of an additional 0.22 mol of NaOH to the reaction mass, continued heating at 95° C. resulted in a conversion of only about 25%. This experiment establishes that the reaction to convert one mol of MHPO to its component (1 mol diisopropanolamine) requires two (2) mol NaOH. A white precipitate formed during the process and was identified by IR analysis as Na2CO3.

Sources & evidence

ORD record
ord-4a294be3bbc6439f9cdb9b8e09a311c1
Source dataset
uspto-grants-1981_07
Patent number
US04281200

Reaction notes

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