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Vijay Kirpalani
CEO : Pi – PROCESS Intensification Exp. LLP
President : Flow Chemistry Society - India
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TOOL - BOX
FLOW CHEMISTRY
&
Downstream Operations
IGCW-2017 – FCS India Conference
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FLOW REACTORs – WHEN ?
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Advantages of Continuous Flow Reactors
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General benefits of continuous systems
1. Smaller equipment, smaller buildings & reduced overall plant footprint
2. Energy savings
• Smaller buildings have lower HVAC costs • Less hardware to heat and cool • Reduced peak loads on process utilities (smaller boilers and chillers)
3. Greater flexibility. A flow reactor can handle a wider range of throughput capacities
4. Improved safety via smaller in-process inventories & easier pressure containment
The other aspect of flow chemistry relates to performance v/s scale
Reducing the reactor size can have a beneficial impact on:
• Heat transfer
• Mixing speed
• Mixing shear
The degree these parameters affect the process/chemistry is application-specific
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Process Challenges
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Synthetic transformations pose many different challenges;
1. Exothermic reaction that is fast & uncontrollable above the lab-scale
2. Multiple reaction phases
3. Sequential reactions that give rise to by-products
4. Biocatalytic processes that fail to scale beyond the lab
5. Production of solids with uniform characteristics
Conclusion: Flow reactors are flexible to multiple processes,
however the right reactor must be selected for the process challenge
Once you have decided to use flow,
how do you select the right flow reactor ?
• What criteria to consider? (45 Key attributes listed in Appendix)
• What reactors are out there?
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What to Consider?
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Based on the SCALE you wish to use in continuous processing,
different aspects may be considered :
Lab-scale: mg-g • Speed • New reaction space • Selectivity • Flexibility
1. What process?
2. What production volume & production rate?
3. Heat & mass transfer requirements
Example: Micro-reactors are not used to produce tonnes & spinning disks not for mg’s
Process R&D: g-kg’s • Speed • Safety • Robustness
Production: kg’s to multi-tonnes • Speed • Safety • Robustness • Cost reduction • Quality
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Key Considerations
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THERMAL CONTROL
MIXING SENSITIVITY
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Key Considerations
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Heat Transfer
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Heat Transfer
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1
10
100
1000
10000
1 10 100
Surf
ace
to
vo
lum
e (m
2/m
3)
Tube diameter (mm)
1
10
100 1000 10000
Surf
ace
to
vo
lum
e (m
2/m
3)
Reactor capacity (litres)
Reduced equipment size delivers higher Heat Transfer Area - to - Volume
Flow
Heat transfer area per unit volume in a tubular flow reactor is 1 to 3 orders of magnitude higher than a typical batch (depending on respective size).
There is however a trade off when using tubes since heat transfer area per unit length suffers as the diameter is increased.
Batch
And then you have the “SYNTHETRON” with S/V ratio = 1,84,000 m2 /m3
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Heat Transfer
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Mass Transfer
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Mass Transfer
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Mixing Time Plug Flow ?
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Mixing time is important if you have;
1. A + B C (desired product)
2. A + C D (impurity)
If the mixing time is short in relation to reaction time, less secondary product is formed since reactant A is consumed more quickly by the primary reaction.
Stirred tank / Batch reactors
In a batch reactor the process material needs to turnover ≈5 times to achieve >99% mixing*. In a large batch reactor
(1,000’s of litres) this is measured in minutes / hours. *Fluid flow in turbine-stirred, baffled tanks-I. Circulation time, Chemical Engineering Science, vol. 19, no. 3, pp. 201–208, 1964
Flow reactor
The mixing path in a flow reactor tube is 1-3 orders of magnitude shorter than a batch reactor.
Mixing times in the millisecond range are seen.
In a flow reactor time relates to distance travelled.
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Plug Flow – Examples
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Plug flow is important if;
• Reactants & products can react to give side products
• Full flushing of the reactor is required
What does this look like in reality?
Assuming no dispersion, a flow reactor behaves like several batch reactors in series
Narrow Residence Time Distribution:
• All molecules experience the same conditions = uniform product quality
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Plug Flow – Examples (2)
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Plug flow increases uniformity of; • Reaction time • Reaction temperature • Product quality
Example: Plug Flow • Plantrix ‘zig-zag’ channel structure has;
• Fully flushed channel • Plug flow = no back-mixing
Fits dispersion model = plug flow
Poor plug flow (high back mixing) has a serious impact on yield, purity and capacity
Bo = 1100
Ref: OPRD, Roder et. al
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Plug Flow – Examples (3)
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Plug Flow – Examples (4)
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Consequence of Back-mixing
• variable reaction time
• variable temperature gradients
• stagnant zones = material can be retained in the reactor ( Product stuck will react with oncoming reactant / will degrade /
disturb the set molar ratios resulting in impurities.)
• Broad RTD (residence time distribution)
• Not problematic for non-consecutive, thermally insensitive or slow reactions ( very few known in organic chemistry)
Turbulent or Poor Plug flow = high back mixing will have a serious impact on yield, purity and working capacity
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Plug Flow – Examples (5)
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Example: Back-mixing ( the heart is NOT Plug Flow)
• Results in variable reaction time & temperature gradients
• Can lead to stagnant zones = material can be retained in the reactor
• Broad RTD (residence time distribution)
• Not problematic for non-consecutive, thermally insensitive or slow reactions
Poor plug flow (high back mixing) has a serious impact on yield, purity & capacity
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High Back-mixing
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Ocillatory Baffled Reactors
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Back-Mixed Reactors are NOT
Flow Reactors !
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BACK-MIXING destroys
PLUG-FLOW
PLUG-FLOW Reactors give excellent MIXING characteristics WITHOUT Back-Mixing.
Back-Mixing & Pulsed Flow (bad pumps) loss of uniform molar ratios & conditions
Result : erratic quality, yields and host of impurities.
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How to Size a Reactor ?
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1
10
100
1000
1 10 100 1000 10000 100000 1000000
Flo
w (
l/h
r)
Reaction time (seconds)
10 ml
100 ml
1 litre
10 litres
100 litres
1,000 litres
Low throughput • Micro reactors
High throughput fast reaction time • Meso reactors • Static mixers • Spinning disk
Volumetric size of a flow reactor (l)= Volumetric flow (l/s) X reaction time (s)
Residence time and volumetric capacity are major factors for choice of flow reactor
High throughput slow reaction time • Oscillatory flow • CSTRs • Stirred / shaken tubes • Spinning disk reactors
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Classifying a Flow Reactor
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90% or more of flow reactors in common use fall within one of 6 basic types and can be classified according mixing and plug flow
Reactor type Mixing method Plug flow method
Micro channels and packed columns
Molecular diffusion and/or static mixing
By default
Meso/large channel plates, tubes & static mixers
Axial velocity with or without static mixing
Axial velocity combined with channel length
PASSIVELY mixed reactors
CSTRs in series Mechanical mixing Random mixing in multiple stages
Stirred / Shaken tube Mechanical mixing Radial mixing combined with channel length
Spinning disk FUMI spinning disk
Oscillatory Flow Tubes (OBRs)
Mechanical mixing Mechanical mixing
Axial velocity bi-directional with static mixing
Controlled mixing in multiple stages -do-
Axial velocity combined with channel length. ( NOT really a Plug Flow reactor)
ACTIVELY mixed reactors
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Materials of Construction
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Depending on the reaction type & process requirements, range of MOC’s are available; • Glass
• Metal (stainless steel, Hastelloy, Tantalum)
• Ceramics (aluminium oxide, silicon carbide)
• Polymers (PMMA, FEP, PFA)
When selecting a reactor material consider; • Chemical resistance
• Thermal requirements (temperature range & heat transfer)
• Pressure requirements
• Feature sizes; • Reaction volume type • Mixing requirement • Overall reactor required
• Process flexibility (toward the future)
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Robust Material of Construction – Silicon Carbide
• Excellent corrosion resistance
– Acids, bases, organics etc.
• High thermal conductivity
• Durable – long lasting
– 50 wt% NaOH at 180 C for 2.5 years – no corrosion
Materials of Construction
Example : Robust Material of Construction – Silicon Carbide
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Integrated Heat Exchange
• Sandwich construction
• Minimal thermal loss
• High thermal conductivity of SiC
– 100-120 W/m2.K at 7 mm
• Maximum control over exothermic reactions
Patented SiC Production Process
• Diffusion bonded – all SiC • No brazing, welds or gaskets
• Metal-free, gas-tight modules
• Monolithic structure NOT sandwiched between 2 SS / Alu Boxes
having Heat transfer fluid !
Patented (EP 637271B1 & foreign patents)
Materials of Construction
Example : Silicon Carbide : Integrated Heat Exchange
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FLOW REACTORS
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TECHNOLOGY PLATFORMS Selection of apt reactor technology platform is most important for better cost benefit realization :- a) HEAT Transfer Area cost -- for Heat Transfer limited process b) Reactor Volume cost -- for Mass Transfer & slow, kinetically limited process
Key types : Pi offers
Micro-reactors / Micro-channel reactors
Falling-film micro-reactors Tubular & “Dynamic-Tubular” flow reactors Spinning Tube-in-Tube reactors Spinning Disk reactors Spinning Disk FUMI reactors Oscillatory Tube/Baffled flow reactors (OBRs) Microwave assisted flow reactors Sonication-assisted flow reactors Multi-cell flow reactors
Aspirator flow reactors, etc.
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Static Flow Reactors
Dynamic Flow Reactors
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PASSIVE MIXING
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Passive Mixing – Micro Reactors
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Passive Mixing - Micro Reactor
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Advantages Applications
Small volume Rapid reaction screening
Flexible MOC’s Available in many MOC’s – adaptable to chemistry
Turnkey systems Accessible for students, training & collection of kinetics
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Passive Mixing - Tube Reactor
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Advantages Applications
Automated Lab-scale reaction screening & g-production
Flexible Versatile MOC’s retain flexibility needed at the lab
Complete system Turnkey system suitable for chemists
E-Series R-Series
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Passive Mixing - Plate Reactor
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Advantages Applications
Very Narrow RTD Reactions needing plug flow
High surface to volume ratio Exothermic reactions (nitrations/oxidations/chlorosulfonations)
Material of construction - SiC Highly corrosive & energetic reactions (120 W/m2.K)
~10 to 400 kg/h
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Passive Mixing – Plate/Tube Reactors
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Passive Mixing – Plate Reactors
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Tantalum Alloyed & SS-316 Plate Reactors (CORROSION Solution)
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Passive Mixing – 3D Printed Reactors
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Titanium, Hastelloy, SS-316L
Marketed by
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ACTIVE MIXING
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Handling Solids in FLOW
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Handling Solids in FLOW
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Handling Solids in FLOW
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Active Mixing – Agitated Tube
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‘Coflore’ – AM Technology
Advantages Applications
Mixing independent of flow rate Slow reactions, multi-phase reactions
Solid/liquid/gas handling Suitable for slurry processing and/or formation
Lab to production scale Screening, feasibility & production
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Active Mixing – OBR / OBC
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‘COBR’ – NiTech
Advantages Applications
Mixing independent of flow rate Crystallisations
Solid/liquid/gas handling Suitable for slurry processing and/or formation
Lab to production scale Controlled crystallisation at pilot & production
CRYSTALLIZERs
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Active Mixing – Spinning Disk
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Advantages Applications
High shear - independent of flow rate
Excellent mixing at a wide flow rate range
Solid handling Precipitations reactions or those using heterogeneous materials
High throughput Tonne-scale production
R-10 16 ml (800 L / day)
SDR-300 230 ml (14,400 L/day)
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Prevent Failures
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Prevent Failures (contd)
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Prevent Failures (contd)
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Murphy’s law : “it anything can go wrong – it will” (someday)
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FDA Support for Continuous Manufacturing:
Review Article Journal of Pharmaceutical Innovation
September 2015, Volume 10, Issue 3, pp 191-199
Modernizing Pharmaceutical Manufacturing:
from Batch to Continuous Production
Lawrence X. Yu and colleagues
Office of Pharmaceutical Quality, Center for Drug Evaluation and Research,
Food and Drug Administration
“…..pharma manufacturers and CMOs should begin to consider the switch
as in the long-run it will end up saving companies time, money and space,
FDA’s Director Janet Woodcock told congressmen in a hearing Thursday.”
http://www.in-pharmatechnologist.com/Processing/FDA-calls-on-manufacturers-
to-begin-switch-from-batch-to-continuous-production
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FDA Support for Continuous Manufacturing
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Advantages
How the characteristics of a continuous flow reactor can affect process parameters
Jones, E, et al Chem.Eng.Res.Des(2012)
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Learning Curve !
It’s high time we understood the precision and accuracy requirements of successful Flow Chemistry practice.
Quite disturbing to see R&Ds playing around with ½” dia coils and old HPLC columns to “practice Flow Chemistry” – is it really any different from the above ?.
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Illustrative Examples
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Lab to Plant in the same equipment
SYNTHETRON
n-BuLi Halex
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n-BuLi Halex API
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GRIGNARD Reaction
Run Grignard reaction continuously in flow without Pump problems
Isolated Yield 89% + E-series
Grignard
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ChemtriX PLANTRIX Micro Reactors made of
EKasic® (SiC) in a pharma API production plant
Grignard Reactions
GRIGNARD Reaction in PlantriX SiC Micro-Channel Reactor
Grignard
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Diazomethane-in 2002!!! • Phoenix Chemicals, UK published their work regarding
continuous flow processing for generating 60 tons per year of diazomethane, while maintaining the inventory of this highly reactive & explosive toxic gas at less than 80g !
Applications in APIs :
• (proceedings of 5th Int’l conference on scale up of chemical processes)
• Phoenix Chemicals, UK published their work regarding continuous flow processing for generating 60 tons per year of diazomethane, while maintaining the inventory of this highly reactive & explosive toxic gas at less than 80g !
Application
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Aromatic Nitration (Plantrix SiC reactor)
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2640 tonne/year
NITRATION
Solvent-free system Highly exothermic
Corrosion resistant SiC
Scale-up Strategy :
Also available
MR-555 upto 4.o Litre
400 Kgs/hour
200˚ C at 25 bar
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NITRATION
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Drivers: Control reaction exotherm (runaway, explosive ) for process safety High “mono- nitro” selectivity , high-productivity & GMP production
DSM selected ChemtriX v/s Corning. Reasons: very few and “secure” connections,
“non-leachable” & “diffusion-bonded” SiC (ChemtriX) v/s Glass or “brazed” SiC (Corning)
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NITRATION
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Aromatic NITRATION in Spinning Disk Reactor (SpinPro)
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Lab Industrial
SpinPro-300
Volume : 270 ml
Reaction time : 5 s
Throughput : 194 kg/h
x2300
Synthetron
Volume : 0.14 ml
Reaction time : 6 s
Highly exothermic, Fast reaction
NITRATION
Throughput : 1550 t/yr
Product : 600 t/yr
in a 270 ml Reactor
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HYDROGENATION with Heterogenous Catalyst in Agitated Tube Reactor
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10,000 tonnes/year ALKOXYLATION Plant
MIPROVA millireactor 0.4 m dia x 7 mt L with 150 reaction channels
1000 L/hr 10,000 tonnes/year
Replaced 20 large batch reactors
Shaoxing Eastlake Biochemical (CHINA)
Fast , highly Exothermic ALKOXYLATION
at AGROCHEMICAL major
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Reactions with Epichlorohydrin in “Coflore”
Drivers: High atom efficiency, Time & Energy conservation, high selectivity and virtually no degradation products (impurities)
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BIOCATALYSIS
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Biocatalysis in “Coflore”
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• Oily starting material
• Lipozyme CalB in water
• ACR-100mL: 7-Fold increase in conversion v/s stirred batch
• Scaling up to ATR-10L gives almost identical, excellent conversion
Biocatalysis in “Coflore”
ESTERIFICATION
0
20
40
60
80
100
0 5 10 15 20 25
Co
nve
rsio
n, %
Reaction Time, h
ATR (1 x 1L tube), 0.25l/min O2
1L Batch, 0.25l/min O2
ATR 10L, 0.75l/min O2
4L batch, 1l/min O2
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Process Intensification
of
DOWNSTREAM
UNIT
OPERATIONS
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Process Intensification Technology Platform
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Unit-Ops -- Extraction
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SpinPro SDE-300
Volume : 300 ml
Throughput : 10,000 L / day +
Extremely High Extraction Efficiency
Drivers: Complete product extraction, ideal for recovery of solvents/organics from waste water, high-productivity & GMP equipment
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Unit-Ops - Extraction/Separation
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Unit-Ops -- Distillation
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Reactor
SplitterExtractive
Distillaton
Solvent
Recovery
Methanol
Recovery
Extractor
Azeo
Column
Decanter
Flash
Column
Color
Column
Flash
Column
Water
Water
Heavies
Methyl
Acetate
Water
Catalyst
Methanol
Acetic Acid
Reactor
Column
Impurity
Removal
Columns
Water
Heavies
Acetic Acid
Methanol
Sulfuric
Acid
Methyl
Acetate
Reactive Distillation
Eastman Chemicals
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Unit-Ops -- Intensified Distillation
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HiGee Distillation
30 mt column replaced by a 1.5 mt column for MeOH Distn.
Drivers: v. high vapour-liquid contact surfaces // v. Low reflux ratios // v. Low energy consumption, v. low space requirements
Potters & Potters
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Unit-Ops -- Crystallization
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Oscillatory Tube Crystallizer
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Unit-Ops -- Filtration
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Modular Spin Disk Filter –Dynamic Membrane
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Unit-Ops -- Absorption
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Pulsed-Jet Dynamic
Waveform Absorber
Drivers: v. high gas-liquid contact surfaces // v. high efficiency // v. low space requirements
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CLOSING REMARKS Process Intensification & Flow Reaction Platforms
1. small footprint & low CAPEX ( a major advantage for sterile-processing & clean-room projects at a fraction of the CAPEX usually required)
2. v. small (and so low cost) Utility CAPEX -- due to v low peak-loads
3. v. high heat transfer area/volume ratios
4. discernable design-space -- QbD built-in
5. reproducible consistent quality & yields (impurity profile is more precise)
6. genuine feasibility for application of PAT (Process Analytical Tools)
7. highly flexible ( key equipments can be plug-&-produce )
8. v. high turn-down ratios ( 1000 : 1 times production capacities)
9. High intrinsic safety due to extremely low reaction volumes, low residence times and high degree of temp/pressure control.
10. easy Lab to Plant scalability
We now see equipments giving 10,000 MT/yr at 1000 ml reaction volume !
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It will be interesting to see how the scene unfolds in INDIA ......
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Thank You
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[email protected] www.pi-inc.co
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Questions/Comments??
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