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Green chemistry in chemical reactions: informatics by design
Alex M. Clark, Ph.D.
July 2015
© 2015 Molecular Materials Informatics, Inc. http://molmatinf.com
MOLECULAR MATERIALS INFORMATICS
Data Capture• Reactions normally drawn for chemists…
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• … rather than computers.
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
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+
MOLECULAR MATERIALS INFORMATICS
Green Metrics4
Process Mass Intensity (PMI) =mass of all reactants
mass of products
E-factor =mass of waste
mass of products
Atom Economy =Σ molecular weight productsΣ molecular weight reactants
• Trivial calculations… if the information is available.
Yield =molar mass of product
molar mass of limiting reactant
MOLECULAR MATERIALS INFORMATICS
Digitally Friendly5
primaryreactant
secondaryreactants
catalyst
solvent
intermediate
byproducts
finalproduct
reagent
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
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MOLECULAR MATERIALS INFORMATICS
Reaction Transforms• Reaction = specific description of experiment
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1 2 34
1 2
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• Transform = the generic form of a reaction
MOLECULAR MATERIALS INFORMATICS
Decision Making10
Prod
uct S
earc
h Re
sults
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%
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
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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...
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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
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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 [email protected]
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 [email protected]