Epichlorohydrin → 2-{[(2-Octyldodecyl)oxy]methyl}oxirane

HRID 1440820Notes

Reaction equation

HRID 1440820 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[CH2:6]([CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:15][OH:16])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[OH-].[Na+]>O>[CH2:1]([O:16][CH2:15][CH:14]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:3]1[O:5][CH2:4]1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 214142-Octyldodecanol

Product 1

HCID 150443182-{[(2-Octyldodecyl)oxy]methyl}oxiraneYield 79.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

The 2-octyldodecyl diglycerol ether emulsifier is prepared as follows. 2-Octyldodecyl glycidyl ether is prepared using the aliphatic glycidyl ether method described above. Approximately 360 g of epichlorohydrin is added to a stirred mixture of about 1.5 kg of 2-octyldodecanol (Jarcol I-20; Jarchem Industries) and about 10 g of stannic chloride. After the resulting exotherm heats the reaction mixture to about 70° C., the mixture is stirred under nitrogen for an additional about 6 hours at about 65° C. About 190 g of sodium hydroxide prediluted in approximately 280 g of distilled water is then added and reacted for about 6 hours at about 65° C. After separating the aqueous layer, the organic layer is water washed three times, heated to about 95° C., sparged with nitrogen to dry, and distilled in the range of about 185°-210° C. and <1 mm Hg to yield approximately 1.1 kg of 2-octyldodecyl glycidyl ether. Approximately 8.1 g of sodium methoxide (25% by weight in methanol) and approximately 1400 g of anhydrous glycerine are reacted together for about 3 hours under nitrogen at about 130° C. After heating the resulting mixture to about 185° C., the 2-octyldodecyl glycidyl ether is added dropwise over a period of about 2 hours. The resultant mixture is stirred for about 4 hours at about 185° C. under nitrogen and then allowed to cool without mixing. A glycerine layer settles to the bottom and is removed by siphoning. Volatiles are distilled from the remaining material by heating to about 150° C. at about 2 mm Hg, yielding approximately 1.3 kg of product. Approximately 700 g of the product is dissolved into an excess of mixed hexanes. This hexane phase is multiply extracted with 90:10 (v:v) methanol:water. The methanol:water extracts are combined and the solvent is removed using a rotary evaporator. The resulting residue is heated to about 70° C. and filtered through a glass microfiber filter, yielding approximately 380 g of 2-octyldodecyl diglycerol ether emulsifier. The product is analyzed by gel permeation chromatography and found to be about 82% diglycerol monoaliphatic ether and about 5% triglycerol dialiphatic ether. The product has a minimum interfacial tension of about 4.8 dyne/cm

Workup

  1. custom2-Octyldodecyl glycidyl ether is prepared
  2. customto about 70° C.
  3. additionis then added
  4. customreacted for about 6 hours at about 65° C
  5. customAfter separating the aqueous layer
  6. washwashed three times
  7. temperatureheated to about 95° C.
  8. customsparged with nitrogen
  9. customto dry
  10. distillationdistilled in the range of about 185°-210° C. and <1 mm Hg

Sources & evidence

ORD record
ord-1cbc2a7516224e37a960de6431cd1be8
Source dataset
uspto-grants-1996_03
Patent number
US05500451

Reaction notes

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