Duisburg Harbour 1963

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Duisburg Harbour 1963
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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
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The E Factor

• Amount of waste/kg product
• Product tonnage E Factor
• Bulk Chemicals 104-106 lt1 - 5
• Fine chemical Industry 102-104 5 - gt50
• Pharmaceutical Industry 10-103 25 - gt100

R.A. Sheldon, Chem Ind,1997,12 1992,903
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Roger Sheldon
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ATOM EFFICIENCY STOICHIOMETRIC VS CATALYTIC
OXIDATION
Stoichiometric The Jones Reagent (Sir Ewart
Jones)
Etheor ca. 1.5
Atom efficiency 360 / 860 42
Catalytic
Atom efficiency 120/138 87 Byproduct H2O
Etheor ca. 0.1(0)
Atom Economy B.M.Trost,Science,1991,254,1471
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The Environmental Quotient EQ

• EQ
  E(kg waste) Q (Unfriendliness
  )
• e.g. NaCl1 ( arbitrary)
• Cr salts 1000?

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CHROMIUM(VI) THE ORGANIC CHEMISTS 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 Its hexavalent chromium, highly toxic,
highly carcinogenic. Gets into your DNA,
so you pass the trouble along to your
kids. Julia Roberts in Erin Brokovich
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CATALYTIC VANILLIN SYNTHESIS RHODIA PROCESS
Overall C6H6O H2O2 CH3OH H2CO 1/2 O2 ?
C6H8O3 3 H2O
S.Ratton, Chem. Today, March / April, 1998, p.33