Urea → 5-Tetradecyloxolan-2-one

HRID 1757920Notes

Reaction equation

HRID 1757920 reaction equation
[C:1]([OH:20])(=[O:19])[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][CH3:18].CC(C)C.NC(N)=O>ClCCCl>[C:1]1(=[O:20])[O:19][CH:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1176UreaHCID 6360Isobutane2×HCID 445639Oleic Acid

Product 1

HCID 103965-Tetradecyloxolan-2-oneYield 8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

One hundred grams of 98% oleic acid were heated in an autoclave at 220° C. for 3 hours in the presence of 10 grams of clay (bentonite), 70 grams of isobutane and 200 grams of 1,2-dichloroethane. Maximum pressure reached was 700 p.s.i. The autoclave was cooled, the isobutane released, catalyst removed by filtration, and the 1,2-dichloroethane removed at a reduced pressure of about 0.05 mm. The crude product mixture was distilled to give 69 grams of distillate and 31 grams of polymerized acids. The monomeric distillate was fractionated by urea adduction to give 53 grams of branched chain fatty acids, 8 grams of straight chain fatty acids and 8 grams of γ-stearolactone. GLC of the straight chain fraction showed it to be mostly saturated. The branched chain acids were C18 by GLC.

Workup

  1. temperatureThe autoclave was cooled
  2. customcatalyst removed by filtration
  3. customthe 1,2-dichloroethane removed at a reduced pressure of about 0.05 mm
  4. distillationThe crude product mixture was distilled
  5. customto give 69 grams of distillate and 31 grams of polymerized acids

Sources & evidence

ORD record
ord-21a6079751cd4719af89d3b0b1bb1141
Source dataset
uspto-grants-1983_02
Patent number
US04371469

Reaction notes

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