bio-based solvents
DESCRIPTION
(Green Solvents James Sherwood)TRANSCRIPT
www.greenchemistry.net
Bio-Based Solvents
StandardisationCertificationIntegration
James [email protected]
OOH
O
www.greenchemistry.net
2025
2010
2005
Proportion ofbio-based products
in each market sector
Bio-based EconomyEC drivers for bio-based products
Commodity Speciality Fine Polymerhttp://www.achema.de/de/presse/http://www.aaechemie.com/html/aae_solvent_information.htmlhttp://ec.europa.eu/enterprise/policies/innovation/policy/lead-market-initiative/biobased-products/#h2-1
European Commission mandated objectives:
Promote bio-based product market
Do so using existing infrastructure
PlasticLubricant
Solvent
Surfactants
Bio-based solvent market share = 1.5%Current capacity = 12.5%
265 million metric tonnes per year
20 MMT
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Bio-based SolventsStandardisation
Performance Bio-based content
HSE Sustainability
Bio-based SolventsFprCEN/TS 16766
At least 25% bio-based carbonProvide data but no threshold values:• Polarity• Volatility• Colour
• Density• Viscosity
No harsher than REACH and GHS/CLP
No extra barriers for bio-based solvents
LCA according to ISO 14040 and ISO 14044
(soon to also be a European standard)
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Bio-based SolventsPerformance
Solvent Polarity Density B.P /°C Viscosity /cP
Ethanol Protic (high) 0.79 78 1.1
Butanol Protic (high) 0.81 118 2.5
Glycerol Protic (high) 1.25 290 954
2-MeTHF Medium 0.85 79 0.5
FAME Medium ~0.9 >250 ~4
Dimethyl isosorbide Medium 1.15 >200 ~5
Solketal Protic (high) 1.07 191 11
Limonene Low 0.84 176 0.9
O
O
H
HO
O
R
O
O
O
OO
OH
OH
OH
OH
OHOH
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Bio-based SolventsBio-based carbon content
www.greenchemistry.nethttp://www.biopreferred.gov/
Bio-based ProductsCertification
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Bio-based ProductsCertification
Minimum bio-based carbon: ≥20%Total organic carbon: ≥50%
Bio-based carbon content determinationTotal bio-based content calculated indirectlyElemental analysis used to verify composition
• ACDV bio-based content analysis certification scheme: www.chimieduvegetal.com/pageLibre000110dd.asp• DIN CERTCO certification of bio-based products: www.dincertco.de/en/dincertco/produkte_leistungen/
zertifizierung_produkte/umwelt_1/biobasierte_produkte/biobasierte_produkte_mehr_nachhaltigkeit.html• Vinçotte ‘OK Biobased’ certification scheme: www.okcompost.be/en/recognising-ok-environment-logos/ok-biobased
Minimum bio-based carbon: ≥20%Total organic carbon: ≥30%
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Bio-based SolventsApplications in organic synthesis
G. Paggiola, A. J. Hunt, C. R. McElroy, J. Sherwood and J. H. Clark, Green Chem., 2014, 16, 2107.
Biocatalytic esterification:
Lipophilic solvents enhance enzymatic catalysis
OH HO
O O
O
> > >
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Bio-based SolventsApplications in organic synthesis
J. H. Clark D. J. Macquarrie and J. Sherwood, Chem. Eur. J., 2013, 19, 5174.
OH
Biginelli reaction:
NH
NH
O
Ph
Ph
O
OPhCHO Urea
O O
O
Tautomerisation of the dicarbonyl enhances the reaction
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Ionic liquids
Acids
Alcohols Polyols
Thank You For Listening
Aprotic solvents
Amines
Dipolar aprotics
ChlorinatedHydrocarbon
Nitro
Ethers Ester Ketones
Nitriles
OH
OH
OHOH
OH
OH OH
OH
OH
O
OH
O
OH
OH
O
OH
OO
OH
O
O
OH
HOOH
Protic solvents
O
O
O
O O
O
O
O
O
O O
Cyrene
James [email protected]
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Bio-based solvent catalogue
Aprotic solvents:
OH
OH
OHOH
OH
OH
OH
OH OH
O
OH
O
OHOH
O
OH OO
OH
O
O
OH
HOOH
Protic solvents
O
O
O
O O
O
O
O
O
O O
CyreneCirca
Limonene
p-Cymene
1-Butanol
2-MeTHFPennakemEucalyptol
EthylalLambiotte & Cie
Methyl laurate
Ethyl acetateDavy/Sasol
Acetoneγ-Valerolactone
Ethanol
2-Propanol2-OctanolArkema
Ethylene glycolPropylene glycolNovance/Oleon
Butyric acid
Acetic acid
Glycerol Glycerol formalGlaconchemie
Lactic acid
Ethyl lactateGalactic
O
O
H
HO
O
OO
OH
SolketalSolvay
Dimethyl isosorbideRoquette
O
O
O