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Our different categories of compounds

Why is preparative organic electrochemistry so rare?

Because it is a combination of two widely different disciplines
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Chlor-alkali electrochemistry
i.e. Cl2-NaOH production in aqueous
solution

- Engineering skills
- Material science
- Membrane technology

Complex multi-step synthesis,
applying many different types
of reactions, most often in
organic solvents

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Known preparative organic electrochemistry processes

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High current density processes

Semi aqueous solution, high productivity,
low added value products

□ Monsanto “electrodimerisation of acrylonitrile”

- intermediate for nylon 6,6
- sole industrial process
~ 300 kt/year at 4.5 kA/m2

□ Asahi Chemical “Kolbe dimerisation”
to make sebacic acid (plasticizers, lubricants,
hydraulic fluids, cosmetics, candles, ... )

- alternative = extraction
- >> 1 kt/year at ~ 3 kA/m2 in MeOH/H2O
- medium added value

Low current density processes

Organic solvents, lower productivity,
higher added value products

□ BASF “ECO process to make of aromatic
aldehydes” (crop protection agents,
fragran-ces, plating additives, UV absorbers, …)

- ~ 3.5 kt/year at 0.3- 0.5 kA/m2
- MeOH as solvent and reagent
- Green chemistry

□ Our development

- high added value products like
 pharmaceutical intermediates
- 0.2- 0.4 kA/m2 in MeOH

Professor J.Y. Nédélec - Electro-organic synthesis Pros and cons

・Key advantages

-Safety procedures : in situ activation of reagent, mediators, catalysts, and
 therefore no hazardous or unstable intermediate and straightforward
 processes (several reactions with no chemical equivalent)
- Green procedures : no “redox” reagent, therefore no by-products
- Usual high functional compatibilities (avoids protection/de-protection steps)
- Easy control of current density (rate control)
- Possible control of the electrode potential (selectivity)
- Easy automation

 

・Limitations

- Specific equipments and basic knowledge (not widespread)
- Surface (2 D) processes, therefore low productivity
- In reduction: use of polar solvent not really compatible with usual membranes
- Lack of engineering investigations

Some extracts from a book on Organic Electrochemistry

- Industrial ElectroOrganic Chemistry by Hermann Putter (BASF)
   BASF has announced that the electrochemical production of aromatic aldehydes
   a core technology for the company”

- In 1988, D. Degner defined some semiquantitative success criteria for
   electrochemical process parameters

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N-acyliminium precursors - Extremely versatile intermediates

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Classes of compounds accessible :

- complex heterocycles
- non natural amino acids
- peptidomimetics

ECO step leading to our key intermediate
Anodic oxidation of N-protected nitrogen containing compounds

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R1 : a lot of variation is accepted R2 : H or R1 + R2 = (CH2)n i.e : cyclic derivatives

Reference : “Organic Electrochemistry” (4th edition), Chapter 15 pp. 570-588, Lund and Hammerich, 2001

Our most inventive contribution in ECO

Usual composition of ECO mixture  →  Substrate –Reagent - Solvent - Electrolyte
Direct anodic methoxylation       →  Substrate - Electrolyte - Reagent = Solvent
Decarboxylative methoxylation     →  Substrate = Electrolyte - Reagent = Solvent                                                                                    But how to make it work?

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Advantages:
- Good yield
- Simple recovery
- Energy consumption less than
1/3 versus external electrolyte

Typical equipment

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   Lab-scale cell
   Anode surface 1 dm2
   Operates at 4-6 A
   ie 100-150 mmol/8h

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   Micro-pilot cell (ElectroSyn)
   Anode surface 16 dm2
   Operates at 20-40 A, continuously if necessary

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   ElectroProdCell
   Anode surface 2 m2
   Operational end of October 2008
   Estimated capacity 2 t/year

List of products (methoxylated products though direct methoxylation)

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Classes of end products : chiral non-natural α-amino acids, almost any
chiral β-amino acids, many chiral amino-alcohols

SWOT analysis of our ECO technology

Strengths:

  • 25 years of experience
  • Patented innovative approaches
  • Downstream chemistry well developed
  • ECO offers unique solutions
  • Very limited number of players

Opportunities:

  • Solvay’s skills in electrolysis
  • ECO is “Green chemistry”
  • Applications of Ionic liquids in ECO

 

Weaknesses:

  • No expertise with corrosion aspects
  • Limited number of electrodes tested
  • No sales & marketing support
  • Only ECO oxidations

Threats:

  • A few big players could overtake us
  • ECO units never fully “multipurpose”
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