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Green chemistry in chemical reactions: informatics by design

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Chemical informatics technology can be of assistance to chemists for describing reactions in numerous ways, including calculating green chemistry metrics such as process mass intensity, E-factor and atom economy. To facilitate this, chemical reactions have to be described in more precise detail than is the norm for most chemists. There are also numerous practical ways to add more green chemistry functionality to lab notebooks, such as enumerating searchable reaction transforms for environmentally favourable reactions, automatically looking up toxicity and hazard information, and others which are mentioned in the slides.

This presentation was given at the Green Chemistry & Engineering conference in 2015 (Americal Chemical Society Green Chemistry Insititute).

Published in: Technology

Green chemistry in chemical reactions: informatics by design

  1. 1. Green chemistry in chemical reactions: informatics by design Alex M. Clark, Ph.D. July 2015 © 2015 Molecular Materials Informatics, Inc. http://molmatinf.com
  2. 2. MOLECULAR MATERIALS INFORMATICS Data Capture • Reactions normally drawn for chemists… 2
  3. 3. MOLECULAR MATERIALS INFORMATICS Data Capture • Reactions normally drawn for chemists… 2 • … rather than computers.
  4. 4. MOLECULAR MATERIALS INFORMATICS Necessary Content • Many useful metrics are easy to calculate if... • Structures for everything: must be fully interpretable (including inorganics) • All components classified • Balanced stoichiometry - all atoms accounted for whenever possible • Multistep reactions should be handled well 3 +
  5. 5. MOLECULAR MATERIALS INFORMATICS Green Metrics 4 Process Mass Intensity (PMI) = mass of all reactants mass of products E-factor = mass of waste mass of products Atom Economy = Σ molecular weight products Σ molecular weight reactants • Trivial calculations… if the information is available. Yield = molar mass of product molar mass of limiting reactant
  6. 6. MOLECULAR MATERIALS INFORMATICS Digitally Friendly 5
  7. 7. MOLECULAR MATERIALS INFORMATICS Digitally Friendly 5 primary reactant secondary reactants catalyst solvent intermediate byproducts final product reagent
  8. 8. MOLECULAR MATERIALS INFORMATICS Quantities 6
  9. 9. MOLECULAR MATERIALS INFORMATICS Quantities 6
  10. 10. MOLECULAR MATERIALS INFORMATICS Green Metrics • Totals for reactants, products & waste • For each non-waste product: yield, PMI, E-factor, Atom-E… always calculated, always recorded 7
  11. 11. MOLECULAR MATERIALS INFORMATICS Reaction Transforms • Reaction = specific description of experiment 8 1 2 3 4 1 2 3 4 • Transform = the generic form of a reaction
  12. 12. MOLECULAR MATERIALS INFORMATICS Convenience • Apply to a molecule... 9 10 g
  13. 13. MOLECULAR MATERIALS INFORMATICS Convenience • Apply to a molecule... 9
  14. 14. MOLECULAR MATERIALS INFORMATICS Decision Making 10 ProductSearchResults Yield PMI E-factor Atom Economy 100% 2.18 1.18 100% 84% 12.49 11.49 93.3% 82% 19.17 18.17 87.4% 100% 8.26 7.26 56.3% 63% 8.93 7.93 73.3%
  15. 15. MOLECULAR MATERIALS INFORMATICS Reference Information • Green solvents: encourage selection of least harmful - environmental impact - toxicity, flammability, etc. • Looking up reactants & reagents in a hazards database would be useful • Likewise for byproducts: criteria for reaction choice 11
  16. 16. MOLECULAR MATERIALS INFORMATICS Implementation • Primary implementation as the GREEN LAB NOTEBOOK app (iPhone, iPad) • Reference databases & transform searching are works in progress • Desktop version currently underway... 12
  17. 17. MOLECULAR MATERIALS INFORMATICS Further Work • Applying & searching transforms, depiction • Curation of green reaction database • Experiment conditions: so far only scheme and ingredients • Improved reaction atom mapping • Solvent applicability prediction (data bound) • Semantic micropublications: URIs everywhere 13
  18. 18. Acknowledgments http://molmatinf.com http://molsync.com http://cheminf20.org Alex M. Clark @aclarkxyz • ACS GCI • Sean Ekins (Green Solvents) • Antony Williams (ChemSpider) • Inquiries to info@molmatinf.com
  19. 19. Acknowledgments http://molmatinf.com http://molsync.com http://cheminf20.org Alex M. Clark @aclarkxyz • ACS GCI • Sean Ekins (Green Solvents) • Antony Williams (ChemSpider) • Inquiries to info@molmatinf.com

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