Green chemistry in chemical reactions: informatics by design

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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Data Capture• Reactions normally drawn for chemists…

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• … rather than computers.


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

+


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


Digitally Friendly5


Digitally Friendly5

primaryreactant

secondaryreactants

catalyst

solvent

intermediate

byproducts

finalproduct

reagent


Quantities6


Quantities6


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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Reaction Transforms• Reaction = specific description of experiment

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1 2 34

1 2

3

4

• Transform = the generic form of a reaction


Convenience• Apply to a molecule...

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10 g


Convenience• Apply to a molecule...

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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%


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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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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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]

Technology

Green chemistry in chemical reactions: informatics by design