1,3-Butadiene → HCID 21277036, compound

HRID 1033978Notes

Reaction equation

HRID 1033978 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4]CC.C=CC=C.C(=O)CCCC.[CH:17](=O)[CH2:18][CH2:19][CH2:20][CH2:21][CH:22]=O.C(=O)CCCCCC>O1CCCC1.CN1CCCC1=O>[CH2:1]=[CH:2][CH:3]=[CH2:4].[CH2:17]=[CH:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

8

Reactant 5

HCID 78451,3-Butadiene5×HCID 8063PentanalHCID 8130HeptanalHCID 115971-Hexene4×HCID 70620Hexanedial

Product 1

HCID 21277036HCID 21277036, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A catalyst solution consisting of 0.019 g Rh(CO)2 (acac) (300 ppm rhodium), 0.99 g Ligand A (14:1 Ligand A to rhodium ratio), 2.2 g N-methylpyrrolidone (as an internal standard), 2 mL 1-hexene, and 25 mL tetrahydrofuran was charged to a 100 mL Parr reactor. Butadiene (2 mL) was charged to the reactor as a liquid under pressure. The reaction was pressurized to 500 psi with 1:1 CO:H2. The reaction rate for 1-hexene and butadiene was determined by monitoring 1-hexene conversion and the formation of butadiene hydroformylation products by gas chromatography. After 20 minutes of reaction, 1-hexene was found to be 84% converted, corresponding to a rate of 1.39 mol/1-hr. Butadiene hydroformylation proceeded at a rate of 1.0 mol/1-hr. After two hours of reaction the solution was analyzed by gas chromatography to determine product composition. Butadiene was 96% converted. The oxo products consisted of 0.7 g valeraldehyde, 0.1 g pentenals, 0.1 g branched dialdehyde, 0.2 g adipaldehyde, and 1.8 g heptanal.

Workup

  1. additionwas charged to a 100 mL Parr reactor
  2. customconverted, corresponding to a rate of 1.39 mol/1-hr
  3. customproceeded at a rate of 1.0 mol/1-hr
  4. customAfter two hours of reaction the solution

Sources & evidence

ORD record
ord-a448d9cb632c4233be54d167e836aba3
Source dataset
uspto-grants-1994_05
Patent number
US05312996

Reaction notes

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