Morpholine → Morpholine 9-octadecenoate

HRID 893774Notes

Reaction equation

HRID 893774 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>>[C:18]([OH:20])(=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 445639Oleic Acid3×

Product 1

HCID 20838052Morpholine 9-octadecenoate

Procedure

An anionic wax-in-water emulsion was prepared as follows. In a 250 milliliter beaker, a mixture of 80 grams of Duroxon H111, a partially oxidized Fischer-Tropsch wax available from Durachem, and 10 grams of Emersol 233, an oleic acid available from Emery Industries, was heated on a hot plate. The mixture was stirred manually with a thermometer until the temperature reached 110° C., by which time a homogeneous wax melt had formed. The melt was treated with 14 grams of morpholine, which reacted with the oleic acid to form the emulsifier, morpholine oleate, and the resultant solution was maintained at a temperature between 110° and 120° C. Meanwhile, 320 grams of deionized water was heated on a hot plate stirrer in a 600 milliliter beaker until the temperature reached 95° to 98° C. The water was stirred using a large magnet so that a deep vortex was formed. Subsequently, the wax melt containing the morpholine oleate was poured in a steady stream into the edge of the vortex of the water at a rate which resulted in complete addition of the wax in about 2 minutes. Following the addition, the resultant almost clear dispersion was stirred at 95° to 98° C. for about 3 additional minutes, and was then transferred to a cold water bath and stirred rapidly for about 3 minutes until it reached a temperature of about 45° C. The almost transparent emulsion was subsequently transferred to a storage bottle and the total weight of the completed emulsion was made up to 400 grams by the addition of deionized water. The emulsion thus formed contained about 20 percent by weight wax and about 6 percent by weight of the emulsifying agent.

Workup

  1. additionIn a 250 milliliter beaker, a mixture of 80 grams of Duroxon H111
  2. customreached 110° C., by which time
  3. customhad formed

Sources & evidence

ORD record
ord-ff5f9e39633c424ea2d62a5bc1bc639d
Source dataset
uspto-grants-1992_06
Patent number
US05126390

Reaction notes

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