1. Duisburg Harbour 1963

2. TU Delft
What does industry want?
An industrial process should proceed in 100% yield and be amenable to operation in a bathtub by a one-armed operator.
John Cornforth

3. The E Factor Amount of waste/kg product:
Product tonnage E Factor
Bulk Chemicals <1 - 5
Fine chemical Industry >50
Pharmaceutical Industry >100
The E Factor
R.A. Sheldon, Chem & Ind,1997,12; 1992,903

4. Roger Sheldon

5. ATOM EFFICIENCY: STOICHIOMETRIC VS CATALYTIC OXIDATION
Stoichiometric: The Jones Reagent (Sir Ewart Jones)
Atom efficiency = 360 / 860 = 42%
Etheor = ca. 1.5
Catalytic:
Atom efficiency = 120/138 = 87%
Byproduct: H2O
Etheor = ca. 0.1(0)
Atom Economy: B.M.Trost,Science,1991,254,1471

6. The Environmental Quotient EQ
EQ E(kg waste) × Q (Unfriendliness )
e.g. NaCl=1 ( arbitrary)
Cr salts= 1000?

7. CHROMIUM(VI): THE ORGANIC CHEMIST’S FAVOURITE OXIDANT
1856 : Attempted synthesis of quinine (W.H.Perkin)
allyltoluidine
quinine
 Led to the serendipitous synthesis of the first synthetic dyestuff mauveine (aniline purple)
2000 : “It’s hexavalent chromium, highly toxic, highly carcinogenic.
Gets into your DNA, so you pass the trouble along to your kids.”
Julia Roberts in ‘Erin Brokovich’

9. CATALYTIC VANILLIN SYNTHESIS: RHODIA PROCESS3 2
solid
catalyst
La phosphate
gas phase
250 C o a q .
Acid catalyst
noble metal
4 steps, all employing a heterogeneous catalyst
Overall: C6H6O + H2O2 + CH3OH + H2CO + 1/2 O2  C6H8O3 + 3 H2O
S.Ratton, Chem. Today, March / April, 1998, p.33