SYNTHESIS OF WILKINSON’S CATALYST,

[RhCl(PPh3)3], AND THE ABSORPTION OH

HYDROGEN BY THE COMPLEX

INTRODUCTION
A catalyst is characterized as a substance that quickens the rate of accomplishing compound
balance, and which can be recovered unchanged at the end of a reaction. Catalytic procedures can
be broadly characterized into two classes: 1) homogeneous catalysis, a procedure where the catalyst
and reactants stay in a similar phase; and, 2) heterogeneous catalysis, where the reactants and
catalyst are in different stages. In most heterogeneous catalytic systems the catalyst is in the solid
phase and the reactants are liquids or gases.

A medication called Ivermectin has been developed to kill parasites, (Infected black flies which can
spread a disease which produces parasites in your skin). Ivermectin is made by selectively reducing
one of the double bonds in Ivermectin, which is a naturally occurring compound. There are several
double bonds in Ivermectin, so how is the correct double bond reduced? This is accomplished using
a catalyst called Wilkinson's catalyst. Wilkinson's catalyst has the formula [RhCl(PPh3)3]
(chlorotris(triphenylphosphone)rhodium(I)). The Wilkinson's catalyst has ability to selectively reduce
alkenes, or double bonds. The selectiveness makes is useful when we need to reduce a specific
double bond in a molecule.

The large size of the molecule is what allows it to selectively reduce the least hindered double bond.
So, even when there is more than one double bond on the molecule, Wilkinson's catalyst will only
reduce the least hindered double bond because that is where the catalyst is able to fit. Wilkinson's
catalyst could be used to reduce a single alkene on a molecule, but typically it is used when there are
multiple alkenes and we only want to reduce one of the alkenes. It is particularly helpful when we
want to selectively reduce the least hindered alkene.

AIM
Is to synthesis the Wilkinson’s catalyst [RhCl(PPh 3)3]

EXPERIMENTAL PROCEDURE
In a 10mL round-bottom flask equipped with a magnetic stirrer bar, add 5mL of ethanol. Attach a
water condenser and place the apparatus on a heating block, then on a stirrer hot plate. Heat the
ethanol below its boiling point (78oC). Remove the condenser for a moment and add 0.15g of PPh 3,
then place it back. Stir until the solid is dissolved. Remove the condenser again, then add 25mg of
RhCl3.H2O and stir. For 30 minutes, heat the solution under heat reflux. Collect the bright shiny red
crystals by suction filtration, while the solution is still hot. Wash the crystals with 1mL portions of
ether (3X) and dry the crystals on the filter by continuous suction.
RESULTS

IR SPECTRUM

SIGNAL WAVENUMBER CM-1 ASSIGNMENT

1 3056.47 C-H stretch
2 1477.66 C=C stretch
3 1431.74 C=C stretch
4 860-680 Fingerprint region
Melting point =
1
H NMR

Signal 1 2
Ratio of signals, number of 18 27
H integration
Chemical shift (ppm) 7.750-7.710 7.410-7.363
Likely environment H1 H2
Multiplicity quartet quartet
No of H on adjacent 1 1
Carbons
Special features (J 4.2 and 3.6 5.1 and 4.5
constants (Hz))

31
P-109Rh is found at -29.00-29.63 cm-1

The 31P-109Rh coupling constant = +29.63 – 29.00 = 0.63 cm -1

Coupling = 0.63 x 300Hz= 189

DISCUSSION
CONCLUSION

ANSWERS TO QUESTIONS
1. A large excess of triphenylphosphine is essential for the prevention of the formation of a
bridged dimer and to further the reduction of the rhodium(lll) species formed initially.

2. Since reduction does not occur in heated ethanol under reflux unless large excess of the
PPh3 is present and sine acetone-water mixtures can be used in place of the ethanol as a
solvent, then the PPh3 is actually the reducing agent.

3.

REFERENCES
 Organometallic Compounds and Catalysis: Synthesis and Use of Wilkinson’s Catalyst, 2013
 https://study.com/academy/lesson/wilkinsons-catalyst-formula-structure-applications.html
 J. A. Osborn, F. H. Jardine, J. F. Young, and G. Wilkinson, J. Chem. Soc. A. 1966: 1711-1732