flowcat -continuous flow reactor system for … singh flowcat... · flowcat -continuous flow...
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FlowCAT - continuous flow reactor system for hydrogenation
screening and small scale production
HEL LimitedLondon, England
HEL IncNJ, USA
HEL IndiaMumbai
HEL Italia Milan
HEL China Beijing
Dr Jasbir Singh([email protected])
HEL Ltd, England
2nd Symposium on Continuous Flow Reactor Technology for Industrial Applications,
3-4 October, 2010Paris
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Terminology in catalytic reactions
� Homogeneous catalysis
� Heterogeneous catalysis
� Fixed bed or Plug Flow (continuous) and stirred/Batch reactors
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Fixed Bed is special case of continuous flow type.
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Terminology in catalytic reactions
� Homogeneous catalysis
� Heterogeneous catalysis
� Fixed bed or Plug Flow (continuous) and stirred/Batch reactors
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Fixed Bed is special case of continuous flow type.
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Crude Mathematical equivalence of flow and batch reactors
Batch Time Residence Time = Volume/flow rateBatch Time Residence Time = Volume/flow rate
Equivalence – time in batch reactor equates to position down plug flow.Changing flow rate changes residence time: corresponds to batch time.
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Closer Mathematical equivalence of Reactors
PFR (plug flow)
Many CSTRs in seriesCo-Current feeds
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Vertical orientation (top-to-bottom)
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Lab-scale flow Systems – Screening and Prep-scale
Screening •Catalyst in small cartridge, very high catalyst loading• Conversion limited by hydrogen solubility (at high conc.)• Typical throughput 1+ g/day
H-cube (Thales-nono) well established in this field. Limited to
hydrogenations and to screening applications only.
Prep-scale • Traditional “tubular” reactor• “Trickle flow” mode demonstrated• High conversion far exceeding solubility limit• Typical throughput 100+g/day
No fully automated product established up to now.
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FlowCAT Package
•Developed to bridge screening and prep-scale needs•Not limited to hydrogenations• Fully software controlled• Does not require high pressure expert for operation
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Trialled at length by Pfizer for hydrogenation applications. Some results to follow.
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flowCAT Feed Section
N2
H2
MFC
HPLC
Pump
Manual valve
Catalyst / glass packing
FilterTr
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P
Reactor
Heater
Tj
Filter
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flowCAT Product Sampling and Collection
Pressure
controlNeedle
valve
GAS
VENT
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SampleSeperation
vessel
Liquid
product
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FlowCAT Typical Specification
• Standard lengths: 15cm (6”)
• Two standard int. diameters: ½” (12mm) or ¼” (6mm)
• Volumes : 2.8ml, 12ml (in hot zone, approx).
• Standard ovens: heated lengths 10 cm
• 100bar/300C standard (higher temperature/pressureoptions)
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options)
•One liquid and one gas feed standard, other combinationspossible.
Not limited to hydrogenations
Not limited to heterogeneous catalytic reactions
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Flow Capacity of Tubular Reactors
Very wide range of flows are possible, subject to pump range and pressure drop across reactor.
Gas and liquid flow rate determines:
• the “pattern” of flow • Gas/liquid mixing and contact with catalyst • Gas/liquid mixing and contact with catalyst • Conversion•Ease of scale up
Flows rates widely selected to favour that “trickle bed” mode.
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Trickle Bed Flow Regime
Most common mode of operation for tubular fixed bed reactors
� Fixed bed of inert and catalyst pellets, former occupying large volume (50% or more)
� Co-current downward flow of gas and liquid
� Leads to gas dispersed, liquid continuous phases around solids
General Plot for
flowCATtypical
General Plot for flow regimeprediction
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Hydrogen plusNitrobenzene/solvent
G/L vol. ratio 20 (100max, gas at NTP)Hydrogen excess typically 1.83 x stoich.
C6H5NO2 + 3H2 C6H5NH2 + 2H2OHydrogenation of (4%) nitrobenzene to aniline
flowCAT performance Testing
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0.25” internal dia.Temperature 30 deg C
1% Pd/C mixed with glass beads4ml packed volume (30% voids)
Catalyst mass 0.1g (0.2 and 0.4g alternates)
Product (Aniline), analysed by GC
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Trickle Bed Flow – Lab ReactorsDiagram below shows likely position of bench scale flow reactors
flowCAT
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flowCATrange
Reported data range
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0.15
0.2
0.25
0.3
0.35
Gas
co
nsu
mp
tio
n (
mm
ol/m
in)
Hydrogen consumption with pressure Hydrogenation of nitrotoluene to aniline
0
0.05
0.1
0 10 20 30 40 50 60 70 80 90 100
Gas
co
nsu
mp
tio
n (
mm
ol/m
in)
Pressure (bar)
H2 Saturation
0.5 ml/min Liquid flow
Hydrogen 1.83 x stoichiometric( = 20 n ml/min)
Catalyst loading 0.1gBed volume 4ml (30% void)
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0.3
0.4
0.5
0.6
Gas
co
nsu
mp
tio
n (
mm
ol/m
in)
Hydrogen consumption with at different substrate flows Hydrogenation of nitrotoluene to aniline
0
0.1
0.2
0 20 40 60 80 100
Gas
co
nsu
mp
tio
n (
mm
ol/m
in)
Pressure (bar)
H2 Saturation
0.5 ml/min
1 ml/min
2 ml/min
Hydrogen 1.83 x stoichiometric(= 20 to 80 n ml/min)Catalyst loading 0.1g
Bed volume 4ml (30% void)
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0.4
0.5
0.6
0.7F
ract
ion
al C
on
vers
ion
Fractional conversion with pressure Hydrogenation of nitrotoluene to aniline
0
0.1
0.2
0.3
0 10 20 30 40 50 60 70 80 90
Fra
ctio
nal
Co
nve
rsio
n
Pressure (bar)
0.5 ml/min
Liquid flow = 0.5ml/minuite(residence time approx 2.4 mins)Hydrogen 1.83 x stoichiometric
( = 20 n ml/min)Catalyst loading 0.1g
Bed volume 4ml (30% void)
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0.2
0.25
0.3
0.35
0.4
0.45
0.5F
ract
ion
al
con
ve
rsio
n
0.92
Hydrogen flow as
fraction of
stoichiometric
Conversion at different gas flows Hydrogenation of nitrotoluene to aniline
0
0.05
0.1
0.15
0 10 20 30 40 50 60 70 80 90
Fra
ctio
na
l co
nv
ers
ion
Pressure (bar)
1.83
4.58
Liquid flow 1ml/minuteCatalyst loading 0.1g
Bed volume 4ml (30% void)
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Comparison with Stirred Reactor Data
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Auto-MATE4 x 100-300ml HP reactors
AUTOLAB 1000ml HP glass reactor
HP Chemscan8 x 16ml reactors
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Up
take
(l)
1.4
1.2
1.0
0.8
0.6
HYDROGENATION 100ml stirred HP autoHYDROGENATION 100ml stirred HP auto--MATEMATE
10 bara
3.4 bara
Catalyst loading approx 1/100th of flow reactor
100 Psi 50 Psi 75 Psi 125 Psi 150 PsiTime (mins)
80 75 70 65 60 55 50 45 40 35 30 25 20 15 10 5 0
Up
take
(l)
0.6
0.4
0.2
0.0
50ml 4% nitrobenzene in decanol, 0.35g Pd/C catalyst – parallel hydrogenations at 40°C, 1500 rpm
Typical residence time in flow tests
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80
100
120
140
160
180
200
Rea
ctio
n t
ime
(min
s)Time to 100% conversion in stirred reactors (5 to 500ml)
40 °C60 °C
Data from three sizes of stirred reactors
0
20
40
60
80
0 2 4 6 8 10 12 14
Catalyst concentration (g/l)
Rea
ctio
n t
ime
(min
s)
4% nitrobenzene Pd/C catalyst, 6.9 bar
Residence time in flow tests
Catalyst conc in flow tests
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Hydrogenation Screening?
H-cube • Hydrogen generation in situ – safety advantage• Low flow only, limited to screening at low conc orsmall scale compound prep (eg med chem)
flowCAT • Needs hydrogen supply – less safe potentially•Low flow version feasible, cartridge designs being tested•Already in use for prep-scale work Can flowCAT be adapted for screening?
.
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Conversion limited by H2 solubility which increases with pressure
Screening with H-cube: Conversion Limited by hydrogen solubility
10% Rh/CPhCHO0.35 M
PhCH2OH
EtOH, 80°C
(courtesy J Hawkins, Pfizer Inc, August 2010)
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0.12
0.14
0.16
0.18
0.2
Hyd
rog
en f
low
Hydrogen added
to maintain operating
pressure, no excess H2
Conversion Limited by Solubility - flowCAT Hydrogenation of nitrotoluene to aniline
0
0.02
0.04
0.06
0.08
0.1
0 20 40 60 80 100
Hyd
rog
en f
low
Pressure (bar)
Gas consumption (mmol/min)Gas Solubility
Gas feed on pressureLiquid flow 0.5ml/minute
Catalyst loading 0.1gBed volume 4ml (30% void)
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FLOWCATContinuous Flow
Reactor
Sample
flowCAT in commercial R+D
■ Controlled by commercial, well established software/electronics, fully developed
■ Ideal for process development and large enough for prep-scale production
■ Possible to integrate with DOE package and optimise totally automatically.
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Reactor
WinISOHELs Reactor Control
Software
Controls Data
STAVEXDoE Software
Package
Set points Results
GCRaw Data
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PAT integration - Real-time monitoring and feed back control
P
GAS VENT (pressure control)
Productfrom flowCAT
In-line sensor (eg FTIR flow cell),almost real-time data
Gas-liquid separation
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Virtually no producthold up (a few ml)
winISO real-time software monitoring
and feed back control
Gas-liquid separation
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Integrating Process/Analytical Data
process data schedule
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chromatogram data analyser
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Process Development Examples using DOE
■ Samples can be taken at each change of operating condition
■Wide range of conditions can be tested, sequentially, without operator involvement (no need to clean reactor after each change)
■ Integrated with Stavex software
Pressure
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Temp
Pressure
Flow rate
STAVEX software
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EXAMPLE 2: Conversion of chloronitrobenzene to chloroaniline
Cl
NO2 NH2
Cl
NH2
H2
Pd/C
H2
Pd/C
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Cl Cl
NO2
H2 Pd/C H2Pd/C
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GC Traces: chloronitrobenzene to chloroaniline
Fractions: 55.8% chloronitrobenzene
15.2% chloroaniline 6.1% aniline
Conditions:P=5bar T=22oC
Residence time=0.5min
min2.5 5 7.5 10 12.5 15 17.5 20 22.5
'mV'
0.02
0.04
0.06
0.08
0.1
0.12
0.14
0.16
AIA1,'VWD' of U:\FLOWCAT\ALEXIS\DATA\EXPERI~1\4-GCSA~1\CLORON~1\EXPERI~1\151220~1\S1\TESTRU~1.D\1.CDF (AIA imported)
7.0
20
8.8
86
13.
310
14.
635
Aniline
Chloroaniline
Chloronitrobenzene
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Fractions: 24% chloronitrobenzene
43.4% chloroaniline
24.2% aniline
Conditions:P=10bar T=61oCResidence time=1.96min
min5 7.5 10 12.5 15 17.5 20 22.5
'mV'
0.02
0.04
0.06
0.08
0.1
AIA1,'VWD' of U:\FLOWCAT\ALEXIS\DATA\EXPERI~1\4-GCSA~1\CLORON~1\EXPERI~1\181220~1\S14\TESTRU~1.D\1.CDF (AIA imported)
7.0
14
8.8
89
13.
302 1
3.51
9
14.
481
AnilineChloroaniline
Chloronitrobenzene
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chloronitrobenzene to chloroaniline (Pressure-residence time)
Low and high pressures yield the better conversions at medium residence times
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at medium residence times
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chloronitrobenzene to chloroaniline (Temp – residence time)
• Conversion favoured bylow temperatures and high
• Chloroaniline reacts to yield aniline at high temperatures
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low temperatures and highresidence times
• Wrong range of conditions selected – go back!
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chloronitrobenzene to chloroaniline (Pressure – residence time)
• mid-range residence time favours chloroaniline
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• High or low residence time favours aniline
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chloronitrobenzene to chloroaniline (Temp – Residence time)
• Mid-range residence time and low temperature favours high yield chloraniline
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• Aniline favoured by high or low residence time
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Sterioselectivity through flowCAT Process Control
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(Example courtesy J. Hawkins, Pfizer Inc, August 2010)
• 100 g hydrogenated with 1 g of catalyst which was still active
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Diastereoselectivity and Conversion vs. Pressure
80
100
120
140
Cis
/ T
rans
Rat
io
50
60
70
80
90
100
Conversion (%
)
0
20
40
60
0 10 20 30 40 50 60 70 80 90 100
Pressure (bar)
Cis
/ T
rans
Rat
io
0
10
20
30
40
Conversion (%
)Increased diastereoselectivity at the higher pressures easily accessible in flow
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flowCAT - CONCLUSIONS
• Bench-scale flow system, industrially proven development
• Wide range of operating conditions
• Controls all important variables and reports progress in real time.time.
• Full integration of third party sensors for PAT
•Low flow version feasible, cartridge designs being tested
•Already in use for prep-scale work
.
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