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Volker Hessel [email protected]
Eindhoven University of Technology
Department of Chemical Engineering and Chemistry
Micro Flow Chemistry and Process Technology
CPAC / ATOCHEMIS Rome Workshop –Rome 25-27 March 2013
Chemical and Process-Design Intensification in Flow - Seen Holistically
Holistic Process Papers’ “The whole is more than
the sum of its parts"
Aristotle (Αριστοτέλης)
“DA VINCI IS GREEN … 1st GPS EDITORIAL 2012
FULL-CHAIN, HOLISTIC VIEWPOINT
Holistic Route Selection
DOW paper; Leng et al. OPRD (2012)
dx.doi.org/10.1021/op200264t
MULTIPLE-ORIFICE RE-DISPERSION
MICROREACTOR AS SOLUTION
● Adapted orifice spacing
● RT = 23 °C
● vRkt = 0.34 ms-1
Illg, T. et al. (2012) Green Chem., 14, 1420 - 1433
C
0.0 0.2 0.4 0.6 0.80
20
40
60
80
100
Co
nvers
ion
an
d y
ield
/ %
Reactor length / m
Conversion tert.-butylhydroperoxide
Conversion pivaloylchloride
Yield tert.-butyl peroxypivalate
T. Illg, V. Hessel et al. Green Chem. 14 (2012) 1420-1433.
T. Illg, V. Hessel et al. ChemSusChem 4, 3 (2011) 392-398.
T. Illg, V. Hessel et al. Chem. Eng. J. 167, 2-3 (2011) 504-509.
CH3 O
CH3
CH3
O-
K+
+CH3
CH3
CH3
O
Cl
CH3
CH3
CH3
O
O
O
CH3
CH3
CH3
-KCl
Multiphase dispersion
THERMAL IMAGING UNDER
REACTIVE CONDITIONS
0 30 60 90 120 150 18020
40
60
80
100Dosing point 2
TBPP formationDosing point 1
KTBP formation
Tem
pera
ture
/ °
C
Reactor length / mm
0 30 60 90 120 150 180
20
40
60
80
100
40 mLmin-1
9 Lmin-1
21 mLmin-1
0 mLmin-1
0
20
40
60
80
100
90004021
Co
nvers
ion
an
d y
ield
/ %
Utility fluid flow rate / mLmin-1
Conversion tert.-butylhydroperoxide
Conversion pivaloylchloride
Yield tert.-butyl peroxypivalate
0
Experimental:
● vRkt = 0.6 ms-1
● t = 2 s
● QUtility = 0, 21, 40, 9000 mLmin-1
• Shortened t
• Increased yield
• Optimum RT at about 40°C
Multiphase dispersion
[1] Azzawi et al. Method for the production of organic peroxide by means
of micro reaction technique, US20090043122, 2009
● 9 Orifices
● 10x52 cm Loops
● RT: 40°C
● YTBPP: 78%
● t: 15 s
● STY: 55600 g/Lh
Micro reactor process [1]
● RT: 10 - 20°C
● YTBPP: 93 % bei ~6 min
● STY: 3600 g/Lh (-10 - 20°C)
3 x 350 L Cascaded batch [1]
● RT: 10 - 20 °C
● YTBPP: 84% bei ~100 min
● STY: 190 g/Lh (8 - 20°C)
● 9 Orifices
● 10x5 cm Loops
● RT: 40°C
● YTBPP: 64%
● t: 1.5 s
● STY: 469000 g/Lh
Reactor length Temperature control Combination
Optimum design
BENCHMARKING FOR
PRODUCTIVITY
Definition of Process Window
p
T
Limitations in T
Limitations in p
Process
window
• The microreactor instrumentation has widened process windows
• Question is still: can we make them bigger?
T
Stouten et al. Aust. J. Chem. 66 (2013) 121
Hessel et al. ChemSusChem(2013) onlineHessel et al. Chem. Eng. Sci. 66 (2011) 1426Illg et al. Bioorg. Medic. Chem.18 (2010)3627
Hessel Chem. Eng. Technol. 32 (2009)1655Hessel et al. Energy Environ. Sci. 1 (2008)467
Hessel Curr. Org. Chem. 9 (2005)765
Pressurized high-T
capillaries
Propel
Coflore
Flowsyn
X-Cube Flash Asia 320
R Series
COMMERCIAL FLOW CHEMISTRY EQUIPMENT FOR HARSH CONDITIONS
HUISGEN CYCLOADDITION–
TEMPERATURE INFLUENCE
0
10
20
30
40
50
60
70
80
90
100
140 160 180 200
69 % 74 %
91 % 78 %
H N
MR
Yie
ld [
%]
Temperature [ºC]
Reaction Conditions
Flow Rate 10μL/min
ζ (min) 10
Solvent NMP
Cu(CH4CN)4BF4 2.50 mol%
Alkyne M 0.23
Azide M 0.23
A. Carlos-Varaz, V. Hessel, T. Noel, Q. Wang ChemSusChem 5, 9 (2012) 1703-1707.
High-T
HANTZSCH DIPYRIDINE SYNTHESIS
- TEMPERATURE INFLUENCE
Diverse syntheses made in flow in a few min; 50 – 70% yield
High-T
FLASH-FLOW PYROLYSIS
D. Cantillo, H. Sheibani, C. O. Kappe
J. Org. Chem. 77 (2012) 2463-2473.
• Flash vacuum pyrolysis (FVP)
- 400−1100°C; high vacuum
• Flash flow pyrolysis (FFP)
- 160−350°C, 90−180 bar
High-T
Solvent
CLAISEN REARRANGEMENT
- SOLVENT
0
10
20
30
40
50
60
70
80
90
100
220 240 260 280 300
Yie
ld [%
]
Temperature [˚C]
High-T
T. Noel, V. Hessel et al. Tetrahedron 69, 14 (2013) 2885-2890.
High-c
CLAISEN REARRANGEMENT
- CONCENTRATION
T. Noel, V. Hessel et al. Tetrahedron 69, 14 (2013) 2885-2890.
High-T
JOHNSON-CLAISEN REARRANGEMENT
- TEMPERATURE
0
20
40
60
80
100
120 140 160 180 200 220 240
Yie
ld [%
]
Temperature [℃]
O
OOH
+O
O
O
O
OO
AcOH
T. Noel, V. Hessel et al. Tetrahedron 69, 14 (2013) 2885-2890.
S. Borukhova, A. Carlos Varas, V.
Hessel, Q. Wang, P. Watts, C. Wiles,
Poster at IMRET12 (2011).
K.A. Swiss, R.A. Firestone, J. Phys.
Chem. A 104 (2000) 3057-3063.
Labtrix 25 bar Home-built 400 bar TU Darmstadt
2000 bar
High-p
PRESSURE IMPACT FOR
1,3 DIPOLAR CYCLOADDITIONS
45
50
55
60
65
70
50 100 150 200 250 300
Co
nvers
ion
(%
)
Pressure (bar)
High-p
CLAISEN REARRANGEMENT
- PRESSURE
T. Noel, V. Hessel et al. Tetrahedron 69, 14 (2013) 2885-2890.
1,2,3-triazole
Prevents Seizures & Lennox–Gastaut syndrome
Proposed route
RUFINAMIDE – TOP-200 BLOCKBUSTER
FIRST RESULTS
- 1,3 DIPOLAR HUISGEN CLICK CHEMISTRY
0.7
0.8
0.9
1
0 20 40 60 80
Co
nvers
ion
[%
]
p [bar]
Huisgen Cycloaddition
Res. Time= 3 min
Flow rate=327 µl/min
Cu-R<1 mol%
T=90 ̊ C
Nucleophilic Substitution
High-p
HIGH-p BATCH RESULTS FOR
RUFINAMIDE FLOW SYNTHESIS
Activity with pressure
Activation volume
High-p
S. Borukhova, V. Hessel, T. Noel, Q. Wang
et al. Green Chem. (2013) to be submitted
M. Busch
1H-NMR FOR REGIOISOMER DETECTION
S. Borukhova, T. Noël , V. Hessel, et al. Green Chem. (2013) to be submitted.
S.C. Stouten, Q. Wang, T. Noël, V. Hessel,Tetrahedron Letters (2013) in press/online
SUPPORTED AQUEOUS
PHASE CATALYST (SAPC)
Base Yield
Et3N 83%
DBU 90%
DABCO 90%
DMAP 19%
pyridine 0%
Base variation
Batch
SAPC – BATCH vs FLOW
PROCESS CHEMISTRY ITEMS
Batch Flow
Product/catalyst separation? Yes Yes
Direct reuse of catalyst? No Yes
Catalyst use per runa 0.4 mol%
(11 mg) 0.01 mol% (0.27 mg)
Catalyst use for a 20 run sequence
0.06 mol%b
<0.001 mol%c
Yield and Reaction time 83% 4 h
21% 2.9 min
S.C. Stouten, Q. Wang, T. Noël, V. Hessel,Tetrahedron Letters (2013) in press/online
10 x [Catalyst]
Soybean Oil Epoxidation –
“NPW in Real World”
B. Cortese, M.H.J.M. de Croon, V. Hessel Ind. Eng. Chem. Res. 51 (2012) 1680-1689.
Oxir
an
e n
um
ber
Time [min]
Oxir
an
e n
um
ber
Time [min]
Simulated
Co
nvers
ion
[%
]
Temperature [C]
Exper.
Dream
Reality
>7
<4
Epoxidation – Pilot Plant
© 03.06.2013
Less harsh conditions were used, and a continuous, faster and able
to work at higher temperature set-up was built at Microinnova.
NPW achieved (after some fight against real world)
1. High-T, large interface
2. Medium-T, medium interface
100 C 70-90 C
0.1
1
10
0.1 1 10
Dif
fusio
n c
oeff
icie
nt
(*10
9)
Viscosity
Anionic Polymerization
– Physically Fully Segregated System = Ideal!
© 03.06.2013
Diffusivity Viscosity
ABD
,
1
ssp
s
s sp
or
2
sp c k c
MW 0.01
0.1
1
10 100 1000
[]
MW [kg/mol]
Viscosity
Dif
fusio
n
co
eff
icie
nt
[x10
9]
MW [kg/mol]
[]
Velocity
Diffusivity
Bringing the NPW to Industrial Production
© 03.06.2013
NPW industrially
achieved
A new continuous, fast
safe process
PDI (flow): 1.04
Residence time [s]
Mo
lecu
lar
weig
ht
Experiment
Simulation
„VERBUND“ INTEGRATION STRATEGY
IN THE SCHELDE DELTA, ANTWERP/B
• Piping interconnection
• Short transportation paths
• Energy integration
• Valued-added chemicals’ chain:
Methionin/Evonik
Aqueous
Phase
Organic
Phase
EDTA (aq)
NMP
Cu
* The European Agency for Evaluation of
Medicinal Products, London, UK, 2002.
Almost complete phase separation
EtOAc
Triazole
Cu?? Syrris, Flexx
module
15 ppm in API is allowed.
A. Carlos-Varaz, V. Hessel, T. Noel, Q. Wang
ChemSusChem 5, 9 (2012) 1703-1707.
3-STAGED Cu SEPARATION IN FLOW
Extraction Stage Residual Copper
start 3156 ppm
1 159 ± 9 ppm
2 97 ± 3 ppm
3 14 ± 1 ppm
Process integration
• EMMA is cheaper + less toxic dipolarophile as
• Not as active under diluted conditions
• Solvent free synthesis results in >80% yield
given 10 min res. time at 200˚C and 70 bar
• Diluents
NMP – 1:6
ACN- 1:10
MeOH- 1:14
• With CAN: 2 g/h at 200˚C and 60 bar
Ease of
purification
S. Borukhova, T. Noël , V. Hessel, et al.
Green Chem. (2013) to be submitted
Process integration
1st STEP: SOLVENT-FREE CYCLOADDITION
AND FURTHER OPTIMZATION
EMMA (methyl trans 3-
methoxy acrylate)
Cyclohexane
KA Oil
Cyclohexene
Adipic Acid
ADIPIC ACID
- DIFFERENT ROUTES
Flow process design
needs reaction design
V. Hessel, I. Vural Gursel, Q. Wang, T. Noel, J. Lang, Chem. Eng. Tech. 35 (2012) 1184
V. Hessel, I. Vural Gursel, Q. Wang, T. Noel, J. Lang, Chem. Ing. Tech. 84 (2012) 660
I. Vural Gursel, V. Hessel, Q. Wang, T. Noel, J. Lang, Green Proc. Synt. 4 (2012) 315
Process integration
Organic phase
Aqueous phase
Syringe pump
Syringe pump
Products
Glass
window
Oil Bath
Thermo-couple
InletOutlet
Inlet
Outlet
T-mixer
90 C, 20 min
n(H2O2): n(cyclohexene):
n(Na2WO4): n(PTC) =
440:100:6.6:1
ADIPIC ACID
- FUNCTION OF OXIDISING STRENGTH
M. Shang, T. Noël, Q. Wang, V. Hessel,
Chem. Eng. Technol. (2013) accepted
H2SO4
90 C, 20 min
n(H2O2): n(cyclohexene):
n(Na2WO4): n(PTC) =
440:100:6:6
ADIPIC ACID
– FUNCTION OF MINERAL ACID
HOOCCOOH
adipic acid
oxidation
Ohydrolysis
H2O
OH
OH
oxidation OH
O
oxidationO
O
OH
oxidationO
O
O
hydrolysis
H2O
M. Shang, T. Noël, Q. Wang, V. Hessel,
Chem. Eng. Technol. (2013) accepted
0
32.9
42
49.5
42.5
31
0
10
20
30
40
50
60
60 70 80 90 100 110 120
Temperature (℃)
Yie
ld
of
ad
ipic
acid
(%
)
Oxidising agent, solvent,
Co-catalyst, PT catalyst,
n(H2O2): n(cyclohexene):
n(Na2WO4): n(PTC)=440:100:6:6
50% H2O2, c(H+) = 1.27mol/l
ADIPIC ACID - PROCESS CONDITIONS
FOR BEST CURRENT YIELD
M. Shang, T. Noël, Q. Wang, V. Hessel, Chem. Eng. Technol. (2013) accepted
90 C, 20 min
n(H2O2): n(cyclohexene)=440:100
50% H2O2 , c(H+) = 0.63 mol/l
ADIPIC ACID - PROCESS CONDITIONS
FOR BEST CURRENT YIELD
PTC
Na2WO4
PTC +
Na2WO4
M. Shang, T. Noël, Q. Wang, V. Hessel, Chem. Eng. Technol. (2013) accepted
ADIPIC ACID – ANALYTICAL
PURITY DETERMINATION
1H NMR
13C NMR
6.5 7.0 7.5 8.0 8.5 9.0 9.5 10.0 10.5 11.0 11.5 12.0 12.5 13.0 13.5 14.0 14.5 15.0 15.5 16.0 min
-25
0
25
50
75
100
125
mVRI
HPLC
PROCESS DESIGN OF THE TRADITIONAL
TWO-STEP & NEW ONE-STEP PROCESS
Process integration ‘2-Step’
‘Direct’
I. Vural Gursel, Q. Wang, T. Noel, V. Hessel, Chem. Eng. Trans. 29 (2012) 565
COST ANALYSIS – ADIPIC ACID P
urc
ha
se
Co
st o
f E
qu
ipm
en
t, M
€
0
5
10
15
20
25
30
35
40
45
2-Step Route Direct Route
Pumps
Compressors
Dryer
Vessels / tanks
Distillation columns
Centrifuges / Filters
Crystallizers
Reactors
Cost Analysis – Adipic Acid
0%
10%
20%
30%
40%
50%
60%
70%
80%
90%
100%
2-Step Route Direct Route
Pumps
Compressors
Dryer
Vessels / tanks
Distillation columns
Centrifuges / Filters
Crystallizers
Reactors
I. Vural Gursel, Q. Wang, T. Noel, V. Hessel, Chem. Eng. Trans. 29 (2012) 565
To
tal P
urc
ha
se
Co
st
of
Eq
uip
me
nt
(Sh
are
of
Co
sts
)
Other
Equip.
Other
Equip.
Reactor
Reactor
Energy Consumption Analysis
Direct Route
Total
Equipment Energy
Consumption, MW
Equipment Energy
Consumption, MW
Reactors Q -119.0 Heat Exchangers Q 28.3
Concentrating Still Qc -93.0 Q 35.0
Crystallizers Q -27.0 Q -2.5
Q -30.0 Dryer Q 4.7
Energy 2-Step Route Direct Route
Power Requirement, MW 4.4 0
Heating Requirement, MW 295.9 68.0
Cooling Requirement, MW 380.6 271.5
Total, MW 680.9 339.5
I. Vural Gursel, Q. Wang, T. Noel, V. Hessel, Ind. Eng. Chem. Res. (2013) submitted
HEAT INTEGRATION – PINCH ANALYSIS
Direct Route
I. Vural Gursel, Q. Wang, T. Noel, V. Hessel, Ind. Eng. Chem. Res. (2013) submitted
HEAT INTEGRATION WITH CONVENTIONAL
AND COMPACT HEAT EXCHANGERS
I. Vural Gursel, Q. Wang, T. Noel, V. Hessel, Ind. Eng. Chem. Res. (2013) submitted
ΔTmin = 10°C ΔTmin = 1°C
Shell-and-tube heat exchanger Micro-/millichannel heat exchanger
Payback time:
7 months (X=50%) Vural Gursel, Chem. Eng.
Trans. 35 (2013) submitted
DIRECT ROUTE – LCA FOOTPRINT
1. AP: acidification potential (average European)
2. GWP 20a: climate change in 20 years
3. EP: Eutrophication potential (average European)
4. FAETP 20a: freshwater aquatic ecotoxicity in 20 years
5. HTP 20a: human toxicity in 20 years
6. Land Use
7. Malodours Air
8. MAETP 20a: marine aquatic ecotoxicity in 20 years
9. High NOx Photochemical oxidant creation potential
10. Depletion of abiotic resources
11. TAETP 20a: Terrestrial ecotoxicity in 20 years Database: Ecoinvent. Source: CML2001
Q. Wang, I. Vural Gursel, M.
Shang, V. Hessel, Energy
Environm. Sci. (2013) submitted
TWO-STEP ROUTE – LCA FOOTPRINT
1. AP: acidification potential (average European)
2. GWP 20a: climate change in 20 years
3. EP: Eutrophication potential (average European)
4. FAETP 20a: freshwater aquatic ecotoxicity in 20 years
5. HTP 20a: human toxicity in 20 years
6. Land Use
7. Malodours Air
8. MAETP 20a: marine aquatic ecotoxicity in 20 years
9. High NOx Photochemical oxidant creation potential
10. Depletion of abiotic resources
11. TAETP 20a: Terrestrial ecotoxicity in 20 years Database: Ecoinvent. Source: CML2001
Q. Wang, I. Vural Gursel, M.
Shang, V. Hessel, Energy
Environm. Sci. (2013) submitted
GLOBAL WARMING POTENTIAL – FOR BOTH
ROUTES AND HYPOTHETICAL SCENARIOS
Q. Wang, I. Vural Gursel, M. Shang, V. Hessel, Energy Environm. Sci. (2013) submitted
HOLISTIC LIFE-CYCLE ASSESSMENT –
REACTION-RELATED GREEN METRICS
Atom Efficiency E-Factor
Q. Wang, I. Vural Gursel, M. Shang, V. Hessel, Energy Environm. Sci. (2013) submitted
Impact category DR
X* = 4.6% DR
X = 40% DR
X = 50% DR
X = 98% CTR
X = 4.6% AP (×10-3 kg SO2) 18.7 13.8 13.8 13.9 48.8
Malodours Air (×104 m3 Air) 16.2 6.7 6.6 6.3 7.0 POCP (×10-3 kg ethylene) 2.7 1.8 1.8 1.8 10.1
EP (×10-3 kg NOx) 11.0 7.5 7.5 7.4 94.7 FAETP 20a (kg 1,4-DCB) 1.9 1.5 1.5 1.3 1.0 MAETP 20a (kg 1,4-DCB) 1.2 0.9 0.9 0.8 0.6
Depletion of abiotic resources (×10-3 kg antimony)
83.7 53.2 53.0 51.0 46.7
TAETP 20a (×10-3 kg 1,4-DCB)
0.3 0.2 0.2 0.2 0.2
Land Use (×10-3 m2) 73.0 58.4 58.9 55.4 41.4 HTP 8.7 7.7 7.8 8.6 5.6
GWP 20a 11.0 6.3 6.3 5.9 6.7
LCA
-Amino alcohols /
Threonine Aldolase
Transesterification /
Lipase (Antarctica)
Gluconic acid /
Glucose Oxidase
REACTIONS INVESTIGATED IN
ENZYMATIC MICROREACTORS
Silicon Dioxide Nanosprings
100 % accessible surface
area (350 m2/g)
Low resistance to fluid flow
Mixed matrix membrane
Absence of mass transfer
limitations
Energy efficiency for
separation
Convenient scale-up
Eupergit
High density of oxirane
groups, operational
stability
Industrial application
SUPPORTS FOR ENZYMATIC
MICROREACTORS
Indirect method
IMMOBILIZATION PROCEDURES
Direct method
Nanosprings
Eupergit
GPTMS method
H. Fu, I. Dencic, V. Hessel et al. Chem. Eng. J. 207-208 (2012) 564-576
-AMINOALCOHOL DIASTEREOMERS
AND ENANTIOMERS
J. Tibhe, T. Noel, Q. Wang, V. Hessel et al.
Chem. Eng. J. (2013) to be submitted
Analytical HPLC
with chiral column, Chirex
3126 (D)-penicillamine column
Enzyme immobilization efficiency
Optimization with incubation time
REACTION RESULTS WITH
THREONINE ALDOLASE
Batch
Stirred
Flow
Immobilized enzyme
Flow
Free enzyme in slug flow
J. Tibhe, T. Noel, Q. Wang,
V. Hessel et al. Chem. Eng. J.
(2013) to be submitted
327 €/genzyme
7321 €/genzyme
225 €/genzyme
I. Dencic, V. Hessel, M.H.J.M. de Croon, J. Meuldijk, C.W.J.
van der Doelen, K. Koch ChemSusChem 5 (2012) 232-245
I. Dencic, J. Meuldijk, M.H.J.M. de Croon, V. Hessel J. Flow Chem. 1, 1 (2011) 13-23
COSTS ENZYME IMMOBILIZATION
Enzyme process cost
value of target product important (gluconic acid – bulk, amino alcohols – high value),
immobilization procedure influences costs, (but also activity)
process optimization to be done.
* Performed at GoNano Technology
Enzyme used β Galactosidase Glucose oxidase Threonine aldolase
Target product galactose* gluconic acid Phenyl ethanolamine
(in 2-step synthesis)
Enzyme immobilized, mg 15 16 2.6
Catalyst cost (€) 17.8 3.6 11.7
Product price (€/g) 0.7 0.3 8.4
Catalyst cost per one run,
€/gprod
2201 37.5 3903
Number of reuses needed 31446 1249 4647
I. Dencic, J. Meuldijk, M.H.J.M. de Croon, V. Hessel J. Flow Chem. 1, 1 (2011) 13-23
Enzyme deactivation
Pressure drop
Target production for pharmaceuticals = 1 – 10 g/h
Mass transfer limitations
Costs
Reactor[a]
Enzyme Support
(mg)
Amount of immobilized
enzyme (mg)
Amount of active
enzyme (mg)
Productivity
(g/h)[b]
GoNano v1 GOx 11.5 7.1 0.71 0.099
GoNano v2 GOx 100 87 6.17 0.397
GoNano v1 TA 17.5 3.51 0.45 0.212
GoNano v2 TA 100 20.1 2.59 1.210
Eupergit TA 133 1.15 0.60 0.280
Membrane TA 750[c]
0.88 0.088[d]
0.041
THEORETICAL POTENTIAL OF PRODUCTIVITY
OF ENZYMATIC MICROREACTORS
H. Fu, I. Dencic, V. Hessel et al. Chem. Eng. J. 207-208 (2012) 564-576.
Amount of enzymes: Flow: 146 g L-1 vs. Batch: 2.4 g L-1
0
0.2
0.4
0.6
0.8
1
0 10 20 30 40 50 60 70 80 90 100
Co
nvers
ion
(-)
Time (min)
(■) Flow reactor; molar ratio: 1 : 2
(▲) Batch reactor; molar ratio: 1 : 5
Productivity: 1.9 g/l 2.86 ml/h; 5 mol/l
FLOW vs. BATCH – LIPASE-NOVOZYM 435
ENZYMATIC MICROREACTOR
I. Dencic, S. van Veen, M. de Croon, J. Meuldijk, V. Hessel et al. Ind. Eng. Res. Dev. (2012) to be submitted
CONTAINER PLANT FOR F3
FACTORY AT INVITE FACILITY
Process Equipment Container (PEC) Process Equipment Assembly (PEA)
Docking Station PEC – BASF/Polymer
PEC – Bayer/Pharma
CONTAINER PLANTS
– POTENTIAL FOR COST REDUCTION?
Lower interest rates
Faster time to market
(“50% idea”)
Wo
rkfl
ow
Ba
sed
on
Mo
du
lar
Co
mp
on
en
ts Process Selection
Modular Assembly Planning
Preassembling Modules
Short Field Installation
Start-up
Optimal Configuration Selection
More efficient embedding of
smart production technologies
Standardized infrastructure: fixed,
small-serial manufacturing costs
Risk depends on capacity risk [%] > risk [%]
NPV ECV
cash
time risk [%]
Compactness
Finechemical Case – Capital Investment
Microreactor operation higher investment cost due to higher cost of more
advanced flow reactor, with 60% yield due to smaller reactor, lower cost
Evotrainer enables ~15% lower capital investment than conventional plant
Evotrainer gives
opportunity for
micro to have
comparable
investment cost
I. Vural Gursel, V. Hessel, Q. Wang, T. Noel, J. Lang, Green Proc. Synth. 1, 4 (2012) 315
Finechemical Case – Operating Cost
Microreactor lower raw material (excess of KHCO3 3 fold instead of 6 fold) and
labour requirement, with 60% yield significant raw material cost reduction
High value product example, raw material cost dominates, Evotrainer effect seen
small
I. Vural Gursel, V. Hessel, Q. Wang, T. Noel, J. Lang, Green Proc. Synth. 1, 4 (2012) 315
Microreactor operation, 60% yield highest cash flow due to lowest operating cost
Evotrainer enables slightly higher cash flow due to investment cost difference
Finechemical Case – Cumulative Cash Flow
Flow optimised
Small-scale flow
Batch
Container Conventional
I. Vural Gursel, V. Hessel, Q. Wang, T. Noel, J. Lang, Green Proc. Synth. 1, 4 (2012) 315
Reduction of risk, construction period – Evotrainer enables ~40% higher NPV
Microreactor operation although higher risk still higher NPV achieved due to lower
operating cost
Fine Chemical – NPV
Flow optimised
Small-scale flow
Batch
Container Conventional
ca. 40%
I. Vural Gursel, V. Hessel, Q. Wang, T. Noel, J. Lang, Green Proc. Synth. 1, 4 (2012) 315
Evotrainer advantageous for fine-chemical and pharma production
Bulk-chemical not profitable at this low production rate
3 Chemical Applications
PAGE 64
Pharmaceutical
Fine-chemical
Bulk-chemical
2,4-dihydroxybenzoic acid
adipic acid
naproxen
All in flow
ca. 25%
I. Vural Gursel, V. Hessel, Q. Wang, T. Noel, J. Lang, Green Proc. Synth. 1, 4 (2012) 315
GREEN PROCESSING & SYNTHESIS
TOPICS
• Sustainable & Green Chemistry, Flow Chemistry
• Advanced, Asymmetric and Bio-inspired Synthesis
• Chemicals from Biomass, White Biotechnology
• Catalysis + Smart Processes for Green (Sustainable) Chemistry
• Green Processing, Novel Process Windows
• Micro Process Technology , Process Intensification
• Alternative Energy (MW, US) and Non-Conventional Media (IL, scF)
• Fuel Cells and Hydrogen Economy
• Photochemistry, Photovoltaics, Energy Storage
• Environmental Chemistry and Toxicology
EDITOR-IN-CHIEF
• Volker Hessel, Eindhoven University of Technology / NL
EDITORS
• Whei Zhang, Boston Center for Green Chemistry / USA
• Galip Akay, Newcastle University Newcastle upon Tyne / UK
• Yi Cheng, Tsinghua University / CN
• Michael C. Cann, University of Scranton / USA
• Isabel Arends, University of Delft / NL
• Dana Kralisch, University of Jena / D
• Giancarlo Gravotto, University of Turino / I
• Christophe Serra, University of Strasbourg / F
• Basu Saha, South Bank Uinversity London / UK
Dr. Q. Wang, Postdoc
T. Illg, PhD
B. Cortese, PhD
P. Tambarussi Baraldi Postdoc
L. Borukhova, PhD
Dr. T. Noel, Assistant professor
I. Vural, PhD
I. Dencic, PhD
S. Stouten, PhD
Acknowledgement to the Group:
Micro Flow Chemistry and Process Technology
S. Van Veen, Master
M. Shang, PhD
B. Spasova, PhD at IMM/TUD
J. Tibhe, PhD
A. Carlos-Varaz Master
H. Fu, Master
A. Hemert, Secretariat
J. Smit, Editorial Assistant
E. Shahbazali PhD