Stearic Acid → 1-Heptadecene

HRID 1461894Notes

Reaction equation

HRID 1461894 reaction equation
[C:1](O)(=O)[CH2:2][CH2:3][CH2:4][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]C.C(OC(=O)CC)(=O)CC.CP(C)C1C=CC=CC=1>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[ClH+][Rh-][ClH+].[Rh]>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 5281Stearic AcidHCID 31263Propionic anhydrideHCID 69597Dimethylphenylphosphine

Product 1

HCID 232171-HeptadeceneYield 639.3%

Reagents, catalysts & solvents 1

HCID 45072191Bis-mu-chloro-tetracarbonyl dirhodium(I)Catalyst

Conditions

Temperature
255 °C

Procedure

In a procedure similar to example 3, a mixture of stearic acid (70.0 g, 0.246 mol), propionic anhydride (16.0 g, 0.123 mol), chlorodicarbonylrhodium (I) dimer (0.48 g, 0.0012 mol), and dimethylphenylphosphine (0.68 g, 0.0049 mol) was heated under reduced pressure (35-45 torr) using an oil bath maintained at 255° C. and the product collected as it distilled from the reactor. The material removed from the reactor was continuously replaced with a mixture of stearic acid and propionic anhydride (4:3 molar mixture, respectively) in a rate that maintained the initial level of the reactor contents throughout the course of the entire reaction. The formation of product ceased after ca. 8 hours of reaction time. The combined distillate product was washed with water and distilled to provide 375 g of 1-heptadecene (bp 140° C./0.6 torr) which was found by GC analysis to be 93.4% of the α-olefin. TON=657.

Workup

  1. temperaturewas heated under reduced pressure (35-45 torr)
  2. customthe product collected as it
  3. distillationdistilled from the reactor
  4. customThe material removed from the reactor
  5. additionwas continuously replaced with a mixture of stearic acid and propionic anhydride (4
  6. temperature3 molar mixture, respectively) in a rate that maintained the initial level of the reactor contents
  7. customthroughout the course of the entire reaction
  8. customThe formation of product ceased after ca. 8 hours of reaction time
  9. washThe combined distillate product was washed with water
  10. distillationdistilled

Sources & evidence

ORD record
ord-4c84e910e9814f108e219f05322153a3
Source dataset
uspto-grants-1991_12
Patent number
US05077447

Reaction notes

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