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www.greenchemistry.netJames.Sherwood@york.ac.uk Rio de Janeiro April 2016
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Solventsproblematic yet indispensable
Cosmetics
Plastics industry
Metal cleaningAgroc
hemica
lsFo
od se
ctor
Dry cle
aningOther industries
Home cleaning
Adhesives
InksPaints/coatings
Pharma
Solvent is the major ingredient (the ‘wet’ bit if you were wondering)
Solvent is needed in manufacturing & processing
Solvent used for washing
Market: 20 MillionTonnes /year
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Solventsproblematic yet indispensable
ReactantsAuxiliariesWaterSolvent
Material use in drug manufacture
ProductWaste
Actual reaction
‘Hidden’ solvent impact
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Solventsproblematic yet indispensable
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Solventsproblematic yet indispensable
WaterSolvent
Product
Historically solvent impact has been
overlooked
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Rational design and applicationof bio-based solvents
www.greenchemistry.netPhoto credit: twitter.com/giuliapigi
Find solvatochromism data at goo.gl/9DKnLL
Why do we need so many solvents?& how to understand why?
N
O
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Ionic liquids
Acids
Alcohols PolyolsOH
OH
OHOHOH
OH OHOH
OH
O
OH
O
OH
OH
O
OH
OO
OH
O
O
OH
HOOH
Protic solvents
OO
OH
OHHO OH N
OHCl:
Solvent mapping
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Aprotic solvents
Amines
Dipolar aprotics
ChlorinatedHydrocarbon
Nitro
Ethers Ester Ketones
Nitriles
O
O
O
O O
O
O
O
O
O O
O
O
O
NH2
O
OO
O
O
O O
O
OO O O
O
O
S4 focus zones: hydrocarbons and dipolar aprotics
Solvent mapping
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Case study 1. Problem: Solvent substitution necessarySafer, renewable hydrocarbon solvents from food waste
p-CymeneLimonene
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>
>
Case study 1. Problem: Solvent substitution necessarySafer, renewable hydrocarbon solvents
G. Paggiola, A. J. Hunt, C. R. McElroy, J. Sherwood and J. H. Clark, Green Chem., 2014, 16, 2107.
OH
HO
O
O
O
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OH
J. H. Clark D. J. Macquarrie and J. Sherwood, Chem. Eur. J., 2013, 19, 5174.
Ln[product selectivity]
Solvent inducedtautomerisation
O
O
O OH
O
O H2N
O
NH2Ph
O
H
NH
NH
Ph
Ph O
O
O
Case study 1. Problem: Solvent substitution necessarySafer, renewable hydrocarbon solvents
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Case study 2. Opportunity: New alternative solventsA bio-based alternative for dipolar aprotic solvents
Image credit:Andrew Hunt
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O
O
O
CYRENE
Case study 2. Opportunity: New alternative solventsA bio-based alternative for dipolar aprotic solvents
Polarity plotcredit: Laurianne Moity
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Thank you!James.Sherwood@york.ac.ukwww.researchgate.net/profile/James_Sherwood2
http://www.slideshare.net/JamesSherwood2blogs.rsc.org/gc/author/sherwoodj
http://www.york.ac.uk/res/s4/twitter.com/S4_Solvents www.york.ac.uk/chemistry/research/green