1-Octene → 1-Octene

HRID 904093Notes

Reaction equation

HRID 904093 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH-]=O.[Rh:11].[PH3:12]>C1(C)C=CC=CC=1>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Rh:11].[PH3:12].[PH3:12].[Rh:11]

Participants

8

Reactant 3

HCID 81251-Octene2×HCID 24404PhosphineHCID 57438224HCID 57438224, compound

Product 4

HCID 81251-OcteneHCID 23948RhodiumHCID 24404PhosphineHCID 19994275HCID 19994275, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The hydroformylation of 1-octene was carried out in the following manner. Approximately 0.019 grams of Rh6 (CO)16 was charged to a 200 ml stainless steel, glass lined pressure vessel equipped with a magnetic stirrer. After introduction of the rhodium carbonyl compound, the phosphine ligand, 12 grams of 1-octene and 21 grams of toluene were added to the pressure vessel. After stirring for about 10 minutes, the contents were preheated to a temperature of about 80° C. or within about 10° of the reaction temperature. The reactor then was sealed and flushed with 200 psi charges of a synthesis gas mixture of hydrogen and carbon monoxide and containing 50% hydrogen by volume. The vessel then was pressured to 750 psi with the synthesis gas. Continuous agitation was maintained and the reaction was observed by recording pressure drop as a function of time. The reaction was terminated at 300 psi after which the contents were analyzed for product conversion. Tables I-III show the results of various hydroformylation runs of 1-octene using various phosphine ligands, rhodium and phosphine concentrations, various phosphine-rhodium molar ratios. In the tables immediately following, L/Rh refers to the molar ratio of ligand to rhodium metal, n/i refers to the molar ratio of normal to iso isomer in percent, conversion refers to the percent of olefin converted to saturated aldehyde including both normal and iso isomer.

Workup

  1. customequipped with a magnetic stirrer
  2. customwere preheated to a temperature of about 80° C. or within about 10° of the reaction temperature
  3. customThe reactor then was sealed
  4. customflushed with 200 psi charges of a synthesis gas mixture of hydrogen and carbon monoxide
  5. additioncontaining 50% hydrogen by volume
  6. customThe vessel then was pressured to 750 psi with the synthesis gas
  7. temperatureContinuous agitation was maintained
  8. customThe reaction was terminated at 300 psi after which the contents

Sources & evidence

ORD record
ord-a2c8fe87791545a9a8b2e4a38c43c800
Source dataset
uspto-grants-1980_10
Patent number
US04230641

Reaction notes

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