renewable chemistries for bio-aromatics de jong.pdfmarket, growth, technology opportunity...
TRANSCRIPT
Renewable
Chemistries for
Bio-Aromatics
Ed de Jong
Jan Kees van der Waal
Not for publication without permission of Avantium Chemicals
Safe Harbor Statement
This document is being furnished to you solely for information purposes and may not be reproduced orredistributed to any other person. This document does not constitute an invitation or offer to sell, or a solicitationof an offer to subscribe for or purchase, investment products or securities, including securities in AvantiumHolding B.V. (the “Company”), and the information provided is not intended to provide a sufficient basis on whichto make an investment decision. The information in this document is subject to change. Securities may not beoffered or sold in the United States absent registration under the U.S. Securities Act of 1933, as amended or anexemption from registration.
No representation or warranty, express or implied, is given as to the completeness or accuracy of the informationor opinions contained in this document and neither the Company nor any of its directors, members, officers,employees, agents or advisers accepts any liability for any direct, indirect or consequential loss or damagearising from reliance on such information or opinions. Past performance should not be taken as an indication orguarantee of future performance, and no representation or warranty, express or implied, is made regardingfuture performance.
This document may include statements that are, or may be deemed to be, "forward-looking statements". Theseforward-looking statements may be identified by the use of forward-looking terminology, including the terms"believes", "estimates", "plans", "projects", "anticipates", "expects", "intends", "may", "will" or "should" or, in eachcase, their negative or other variations or comparable terminology, or by discussions of strategy, plans,objectives, goals, future events, intentions, beliefs or expectations. Forward-looking statements may and often dodiffer materially from actual results. Any forward-looking statements are based on and reflect the Company’scurrent plans, estimates and projections as well as its current view with respect to external conditions and futureevents; any forward-looking statements are subject to risks relating to future events and other risks, uncertaintiesand assumptions relating to the Company’s business, results of operations, financial position, liquidity,prospects, growth or strategies. Forward-looking statements involve inherent risks and uncertainties and speakonly as of the date they are made.
The Company expressly disclaims any obligation or undertaking to update, review or revise any forward lookingstatement contained in this document whether as a result of new information, future developments or otherwise.
2
3
Avantium, a Leading Renewable Chemicals
Technology Company
Strong shareholder
base with strategicand financial
partners
Now listedTicker: AVTX
capital raised
€200+m
Future
Renewable Chemistries
2013
2012
2011 2010
2014
160100+
patent families
Founded in 2000
In Amsterdam 20+nationalities
Private Company IPO of 15-Mar-2017
employees
Multiple strategic routes to valorize
Renewable Chemistries projects
Lab scalePilot
plant
Reference
plantIndustrial scale
Sale of
products
Licensing
Licensing
Scale
Business
modelSale of
products
Geleen (YXY by Synvina)
Delfzijl (Zambezi by Avantium)
Geleen (Mekong by Avantium)
Bergen op Zoom (Scelio-4B & BIO-HArT*)
Pilot PlantsReference Plant
Antwerp (YXY by Synvina)
4Not for publication without permission of Avantium Chemicals
Hurdles for scale bio-based chemicals adoption
Economics: inefficient (vs. petro-based) conversion routes
Sustainability: need also 2G supply for long term sustainability
Quality: no cost competitive high-purity 2G-glucose available
Technology push: Integration of Innovation catalysis and process in collaboration with all stake-holders
Renewable ChemistryOur vision
Theoretical yield from sugar
67%29%
FD
CA
(P
EF
)
87%
ME
G (
via
Hyd
rog
en
oly
sis
)
103%46%
5
Diels-Alder Novel routes to bio-based specialty Aromatics
Multi-step process to produce drop-in bio-aromatics
Wide Application potential
Diels-Alder using FuranicsFuransCarbo-
hydrates
Aromatization and OxidationDiels-Alder
6
automobile interiors and products
resistance to high temp.
fire-resistant material (Nomex),
resins for drink bottles,
high-perform. polymer (polybenzimidazole)
dyes, perfumes, pharmaceuticals
plasticizers and synthetic fibers
Examples:
R1 R1
R2
R3
OH R1
R2
R2R2
R1
R3
di-, tri-, tetra- aromatics, phenols
Not for publication without permission of Avantium Chemicals
7
O
R2
R1
O
O
O
O
O
O
CO2H
O
O
O
CO2H
CO2H
O
O
O
O
O
OO
O
O
O
O
O
O
O
O
CO2H
CO2H
O
O
O
CO2H
O
O
O
CO2H
CO2H
CO2H
CO2H
CO2H
CO2H
CO2H
CO2H
CO2H
CO2H
CO2H
CO2H
CO2HO
O
OO
OMe
CO2H
CO2H
CO2H
CO2H
CO2H
CO2H
CO2H
CO2H
R1 /R
2 = H
R 1 /R 2
= CO2H
R1 = M
e, R2 =
H
R1 /R
2 =
Me
R1 /R
2 = CO2H
R1 =
Me,
R2 =
H
R1 /R
2 = M
e
R 1/R
2 = H
R1 =
CO 2H, R
2 = H
R 1 = CO
2 H, R 2 = H
Dienophile
CO2H
CO2H
CO2H
CO2H
CO2H
CO2H
CO2H
CO2H
IPA
TMA
HMA
MPA
CO2H
O
O
O
TMA
TBCA
CO2H
CO2H
CDA
HTMA
Market, Growth, Technology Opportunityreplacement of phthalics
Global phthalic anhydride market size was estimated at USD 6.90 billion in 2013. The increasing use
of phthalate plasticizers in automotive manufacturing coupled growing automotive industry is expected
to drive demand over the forecast period.
• Plasticizers (56 %):
• Unsaturated polyester resins (17 %):
• Alkyd resins (17 %):
• Intermediate in the production of (10 %):
─ - polyester polyols
─ - isatoic anhydride
─ - intermediates for pigments and dyes
─ - flame retardants for polyesterpolyols
─ - intermediates in the agricultural and
pharmaceutical sector
9
http://www.grandviewresearch.com/industry-analysis/phthalic-
anhydride-market
http://www.inchem.org/documents/sids/sids/85449.pdf
http://www.orbichem.com/userfiles/CNF%20Samples/pht_13_11.
Process scheme
8/16/2017
10
Diels-Alder
reaction
Hydrogenation
Aromatics
(intermediates)
1st GenAromatics
(full oxidized)
Strictly Confidential
Diels-Alder
reaction+
1St Generation Diels-Alder aromatics
Direct Aromatization route 1
M.S. Newman, (a) J. Am. Chem. Soc., 1944, 66, 733, (b) J. Med. Chem., 1964, 7, 466
Toste et al., Chem. Eur. J. 2011, 12452-12457
o multi-step reaction sequence
o Final aromatization in H2SO4 with low yields
o DA addition, oxidation, dehydration and decarboxylation
1St Generation Diels-Alder aromatics
Direct Aromatization route 2
12
C. Luke Williams, et al., ACS Catal., 2012, 2, 935-939
Zeolite H-Y (Si/Al 30)
o 75% selectivity to p-xylene
o C2H4 57 bar, at 300 oC in Heptane
Zeolite H-BEA (Si/Al 12.5)
o 90% selectivity to p-xylene
o Conditions: C2H4 62 bar, at 250 oC in
Heptane as solvent
C. C. Chang, et al., Green Chem., 2014, 16, 585-588
High pressures are needed for the
unreactive ethylene to react.
The high temperature for
dehydration is against the D-A
equilibrium
Key points
• Starting adduct conversion
100%
• Total aromatics 84%
• Mass balance 90%
H.C. Genuino, J.C. van der Waal, E. de Jong, et al. ChemSusChem. 2017 Jan 10; 10(1): 277–286.
2nd Generation Diels-Alder aromatics
Indirect Hydrogenation route
Co-Mn-Br Oxidation of Substrates
8/16/2017
14
Substrate Structure Yield %
(Selectivity %)
3-Methyl phthalic acid 74 (79)
2,5-Dimethyl benzoic acid 87 (95)
o-Toluic acid 100
M-Toluic acid 93 (93)
3-Methyl phthalic
anhydride
89 (96)
Strictly Confidential
Conclusions
Furfural and other furans will become widely
available, presumably at lower costs
Diels alder chemistry opens the route to a wide
array of products
Reactions are quite selective
Molecules with novel functionality can be made
Smaller scale (tens of kilotonnes) commercial
production is foreseeable with competing prices
for the resulting products
15