2014 boston flow congress presentation heather graehl
TRANSCRIPT
![Page 1: 2014 Boston Flow Congress Presentation Heather Graehl](https://reader036.vdocument.in/reader036/viewer/2022081403/554a3d40b4c90582328b4e32/html5/thumbnails/1.jpg)
Flow Chemistry: A useful method for performing hazardous chemistry in a safer manner
Heather Graehl, MS, MBA [email protected]
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Who are we?
• ThalesNano is a technology company that gives chemists tools to perform novel, previously inaccessible chemistry safer, faster, and simpler.
• Based Budapest, Hungary • 33 employees with own chemistry team. • 11 years old-‐most established flow reactor company.
• R&D Top 100 Award Winner.
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• Flow Chemistry Market Leader • Over 800 customers worldwide
Customers
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What is flow chemistry?
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Performing a reacQon conQnuously, typically on small scale, through either a coil or fixed bed reactor.
OR
Pump Reactor CollecQon
What is flow chemistry?
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Flow reactors can achieve homogeneous mixing and uniform hea6ng in microseconds (suitable for fast reac6ons)
Improved Mixing Compared to Batch
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Improved mixing can lead to improved reac6on 6mes, especially with fixed bed reactors
Improved Mixing = Faster Rxn Time
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• Microreactors have higher surface-‐to-‐volume raQo than macroreactors, heat transfer occurs rapidly in a flow microreactor, enabling precise temperature control.
Yoshida, Green and Sustainable Chemical Synthesis Using Flow Microreactors, ChemSusChem, 2010
Enhanced Temperature Control
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Exothermic Chemistry – LiBr Exchange
• Batch experiment shows temperature increase of 40°C. • Flow shows little increase in temperature.
Ref: Thomas Schwalbe and Gregor Wille, CPC Systems
Exothermic ReacQons
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Batch Heated Rxns • Safety concerns, especially in scale
up
• Microwave technology is fastest way of heaQng solvent in batch
Flow Chemistry Heated Rxns • Flow mimics microwave’s rapid
heat transfer
• Solvent is not limited to dipole
• Higher pressures and temperatures possible
• High pressures allow use of low boiling point solvents for easy workup
• Safety improvement as small amount is reacted, conQnuously
Endothermic ReacQons
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Discovery Scale: ! Making processes safer ! Accessing new chemistry
! Speed in synthesis and workup
! AutomaQon
Process Scale: ! Making processes safer ! Reproducibility-‐less batch to batch variaQon
! SelecQvity ! Green
Why move to flow?
Survey Conducted
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Where is flow chemistry applied best?
Exothermic Reactions • Very good temperature control • Accurate residence time control • Efficient mixing • Less chance for thermal run-away • Higher productivity per volume • High selectivity
Endothermic Reactions • Control over T, p and residence time • High selectivity • Accessing new chemistry • Higher productivity per volume • High atom efficiency
Reactions with gases
• Accurate gas flow regulation • Increased safety • Easy catalyst recycling • High selectivity • Higher productivity per volume
Scale up
• Increased safety • Higher productivity per volume • Selectivity • Reproducibility
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150°C, 100 bar (1450 psi) H2, CO, O2, CO/H2, C2H4, CO2. Reactions in minutes. Minimal work-up.
-70 to +80C O3, Li, -N3, -NO2
Safe and simple to use. Multistep synthesis. 2 step independant T control. Coming: fluorinations, low T selectivity
450°C, 200 bar (2900 psi) New chemistry capabilities. Chemistry in seconds. Milligram-kilo scale Solve Dead-end chemistry. Heterocycle synthesis Supercritical Fluids
H-Cube Pro & Gas Module: Reagent gases
Phoenix Flow Reactor: Endothermic chemistry
IceCube: Exothermic Chemistry
Reactor Pla]orms
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H-Cube Hydrogenation and Flow Catalysis Platform
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• HPLC pumps continuous stream of solvent • Hydrogen generated from water electrolysis • Sample heated and passed through catalyst • Up to 150°C and 100 bar. (1 bar=14.5 psi)
Hydrogenation reactions: ! Nitro Reduction ! Nitrile reduction ! Heterocycle Saturation ! Double bond saturation ! Protecting Group hydrogenolysis ! Reductive Alkylation ! Hydrogenolysis of dehydropyrimidones ! Imine Reduction ! Desulfurization
H-‐Cube – How it Works
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Water Electrolysis
Hydrogen Tanks are Explosive and Severe Safety Hazard
Hydrogen generator cell ! Solid Polymer Electrolyte ! Single Cell output:
30ml/min hydrogen
High-pressure regulating valves
Water separator, flow detector, bubble detector
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• Benefits • Safety • No filtration necessary • Enhanced phase mixing
• Over 100 heterogeneous and Immobilized homogeneous catalysts
10% Pd/C, PtO2, Rh, Ru on C, Al2O3 Raney Ni, Raney Co Pearlmans, Lindlars Catalyst Wilkinson's RhCl(TPP)3 Tetrakis(TPP)palladium Pd(II)EnCat BINAP 30
• Different sizes • 30x4mm • 70x4mm (longer residence time or scale up)
• Ability to pack your own CatCarts • CatCart Packer (with vacuum) • CatCart Closer (no vacuum)
Catalyst System -‐ CatCarts
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• Improved H-Cube • 20mg-50g/day • 10°C to 150°C • H2 production variability from 0ml/min – 60ml/min (selectivity!) • Reaction timer with auto switching valves • Software for logs, graphs, reaction guide, module control
H-‐Cube Family
• Improved H-Cube • 20mg-50g/day • -10°C to 150°C • H2 production variability from 0ml/min – 60ml/min (selectivity!) • Reaction timer with auto switching valves • Software for logs, graphs, reaction guide, module control
H-Cube®
H-Cube Pro™ H-Cube Mini™ H-Cube Midi™
Industry Hydrogenations and General Flow Platform
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• Flow rate: 0,3-‐3 mL/min
• Temperature: 25°C to 100°C
• Pressure: 1-‐100 bar
• 30-‐70 mm CatCarts used
• Reusable drying CatCart applied
• 1 hydrogen cell
• Hydrogen producQon: 0 or 22 mL/min
• Small footprint, compact design
• Touch screen graphical user interface
• University teaching material ! Lab Manual ! Lecture Material ! Video
New H-‐Cube Mini for Academia
H-Cube Mini DryCart
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• Installed with hundreds of H-Cubes • Flow Rates: 0.001 to 10ml/min • Stainless steel pump head
• Complaints • Loses prime frequently • Does not tolerate air bubbles • Difficult to maintain • Check valves are not robust • Poor performance at low flow rates, not advisable below 0.5ml/min
„Knauer Pumps are the achiles heel of the H-Cube” – H-Cube Customer
New ThalesNano Micro HPLC Pump
Knauer Smartline HPLC Pump
• New pump for H-Cube and Phoenix • Ruby Ball/Saphire Seat Check Valves • More accurate • Tolerates air bubbles • Self flushing compartment • Less often and easier maintenance • Stainless Steel
New ThalesNano Mirco HPLC Pump
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• Versatile: Compressed Air, O2, CO, C2H4, SynGas, CH4, C2H6, He, N2, N2O, NO, Ar.
• Fast: Reactions with other gases complete in less than 10 minutes
• Powerful: Up to 100 bar capability.
• Robust: All high quality stainless steel parts.
• Simple: 3 button stand-alone control or via simple touch screen control on H-Cube Pro™.
Gas Module
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" Conditions: 100oC, 30 bar, CO gas, 0.5 ml/min liquid flow rate, 0.01 M in THF " Catalyst: Polymer supported Pd(PPh3)4 " Reaction was repeated " Different gas flow rates were tested
Observed reproducible conversion at each gas flow rate
CarbonylaQons
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Pressure Temp. (oC) CatCart Conversion Selectivity
40 25 1 % Au/TiO2 0 – 40 65 1 % Au/TiO2 6.5 >85 40 25 1 % Au
/Fe2O3 0 – 40 65 1 % Au
/Fe2O3 12.7 0 40 25 5 % Ru
/Al2O3 2.8 ~100 40 65 5 % Ru
/Al2O3 3.6 ~100 100 65 5 % Ru
/Al2O3 2.7 ~100 100 100 5 % Ru
/Al2O3 8.5 ~100 100 140 5 % Ru
/Al2O3 15.5 ~100 100 65 1 % Au/TiO2 5.6 84 100 100 1 % Au/TiO2 47.2 93 100 140 1 % Au
/TiO2 ~100 93 100 65 1 % Au
/Fe2O3 4 0 100 100 1 % Au
/Fe2O3 31 7 100 • Area% of desired product in GC-MS / (100 – Area% of reactant in GC-MS)
General conditions: H-Cube Pro with Gas Module, 50 mL/min oxygen gas, 1 mL/min liquid flow rate (0.05M in acetone, 20 mL sample volume), CatCart: 70mm., 1 % Au/TiO2 (cartridge: 70mm, THS 01639),
Batch ref.: Oxygen; perruthenate modified mesoporous silicate MCM-41 in toluene T=80°C; 24 h; Bleloch, Andrew; et al. Chemical Communications, 1999 , 8,1907 - 1908
Very fast addition of alcohol to gold surface. Alkoxide formation.
Green OxidaQon OpQmizaQon
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Powerful: Up to 450°C
Versatile: Heterogeneous and homogeneous capabilities.
Fast: Reactions in seconds or minutes.
Module for H-Cube Pro Use H-Cube’s HPLC pump
and backpressure regulator
Standalone Version Add our new 200 bar
backpressure regulator and Micro HPLC Pump
Safe – Software emergency shutoff and hardware pressure release valve
Phoenix Module or Flow Reactor
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• Choice of stainless steel, teflon, or Hastelloy
• Different length coils to vary residence time
• Easy to recoil
Phoenix Homogeneous ReacQons
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• Use same H-Cube Pro or Midi CatCarts
• Phoenix metal-metal Catcarts for >250°C reactions
Phoenix metal-metal CatCarts (125mm/250mm)
H-Cube Pro CatCarts (30 or 70mm)
Phoenix Heterogeneous ReacQons
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• Standard benzannulation reaction • Good source of:
• Quinolines • Pyridopyrimidones • Naphthyridines
→ Important structural drug motifs
Disadvantages: • Harsh conditions • High b.p. solvents • Selectivity
W. A. Jacobs, J. Am. Chem. Soc.; 1939; 61(10); 2890-2895
High Temp Chemistry – In Batch
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• Replacement of diphenyl ether (b.p: 259°C) with THF (b.p.: 66 °C)
Cyclization conditions: a: 360 °C, 130 bar, 1.1 min b: 300 °C, 100 bar, 1.5 min c: 350 °C, 100 bar, 0.75 min
Pyridopyrimidinone Quinoline
No THF polymerization!
Batch conditions: 2 hours
Gould Jacobs ReacQon -‐ Overview
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• Reactions from 10-450C and 1-100bar (1450 psi) • Up to 13 different reagent gases • Heterogeneous or homogeneous catalysis
Fully Automated system available
VersaQle Catalysis System
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IceCube for
High Energy
Reac6ons
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Halogena6on
Nitra6on Azides
Mul6step reac6ons
Reac6ve Intermediates
Lithia6on
Ozonolysis
Swern Oxida6on
IdenQfied ApplicaQons
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• 2pcs rotary piston pumps, PeristalQc opQon
• 2pcs 3-‐way inlet valves
• Flow rate: 0.2 – 4.0 mL/min
• Max pressure: 6.9 bar
• Main reactor block temp: -‐70/50°C – +80°C
• Main reactor volume up to 8 mL
• Tubing: 1/16” or 1/8” OD PTFE
• Secondary reactor block temp.: -‐ 30 – +80°C
• Secondary reactor volume up to 4 mL
Cooling Module
• ConQnuous ozone producQon
• Controlled oxygen introducQon
• Max. 100 mL/min gas flow
• 14% Ozone producQon
Pump Module Ozone Module
Modular for a Variety of Chemistry
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Welcome screen of the IceCube
Ozonolysis set-‐up 3 pump – 2 reactor set-‐up
Control Module
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First Reac6on Zone Second Reac6on Zone
Water inlet and outlet
Reactor Plate • Aluminum blocks lined with teflon tubes • Easy to coil for desired pre-‐cooling and desired residence Qme amer mixing • Different mixers types available
A B
D
-‐70-‐+80ºC -‐30-‐+80ºC
C First Reac6on Zone Second Reac6on Zone
Cooling Module
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A
B C
A B
C
D
Pre-‐cooler/Mixer Reactor
-‐70-‐+80ºC
-‐70-‐+80ºC -‐30-‐+80ºC
Ideal for reactive intermediates, quenching, or multistep reactions
Single or MulQ-‐Step ReacQons
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What is ozonolysis?
• Ozonolysis is a technique that cleaves double and triple C-C bonds to form a C-O bond.
• Currently neglected oxidation technique • Highly exothermic, ozonide accumulation is dangerous
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Carboxylic Acid (oxidative work-up)
Aldehyde/Ketone (simple quenching)
Alcohol (reductive work-up)
Workup Determines Product
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• Highly effective oxidation • In line quenching of ozonide – SAFETY • Efficient cooling for exotherm control - SAFETY • The reactions typically go cleanly in high yield and
conversion with little by products • Gas is used as a reagent, so work up is less labor
intensive • Ozonolysis is fast and atom efficient • Ease in Scale Up
Why Ozonolysis in Flow?
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Oxida6on of alkynes
Oxida6on of amines to nitro groups
Flow Ozonolysis
M. Irfan, T. N. Glasnov, C. O. Kappe, Org. Leq.,
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Batch reac6on: Max. -‐60°C to avoid side reacQon
In Flow:
Even at -‐10°C without side product formaQon
0.45 M in DCM, 0.96 mL/min
0.45 M alcohol, 0.14 M DMSO in DCM 0.94 mL/min
3.6 M in MeOH, 0.76 mL/min
* Amer purificaQon
When compared to batch condiQons, IceCube can sQll control reacQons at warmer temperatures due to beqer mixing and more efficient heat transfer.
Swern OxidaQon
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• 2 Step Azide Reaction in flow • No isolation of DAGL • Significantly reduced hazards
TKX50
Making Azide Chemistry Safer
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Entry Vflow (ml/min) A -‐ B -‐ C
T (°C) τ (1. loop, min)
τ (2. loop, min)
Isolated Yield (%)
1 0.4 0 2.12 3.33 91
2 0.9 0 0.94 1.48 91
3 0.6 0 1.42 2.22 85
4 0.9 10 0.94 1.48 85
5 1.5 10 0.56 0.88 86
6 1.5 15 0.56 0.88 98
7 1.2 15 0.71 1.11 84
8 1.8 15 0.47 0.74 86
Aniline HCl sol. Pump A
Pump B NaNO2 sol.
Pump C
Phenol NaOH sol. • Most aromaQc diazonium salts
are not stable at temperatures above 5°C • Produces between 65 and 150 kJ/mole and is usually run industrially at sub-‐ambient temperatures • Diazonium salts decompose exothermically, producing between160 and 180 kJ/mole. • Many diazonium salts are shock-‐sensiQve
DioaziQzaQon
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• LithiaQon experiments
• HalogenaQons/FluorinaQons
• Low temperature selecQve reacQons, not necessarily
exothermic nature
• EpoxidaQons
Coming soon…
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Our chemistry team is full of flow chemistry and catalysis experts
We aim to solve your challenging chemistry in flow!
Phoenix Flow Reactor - High temperature and pressure reactor for novel heterocycle and compound synthesis (up to 450C)
H-Cube Pro and Gas Module - for gas reagent chemistry from hydrogenation to oxidation
IceCube - for low temperature and high energy reactions
Free chemistry services on Thalesnano flow platforms for up to a week. No strings attached.
Ship us your compound or visit our labs in Budapest, Hungary. CDAs and NDAs are approved quickly.
Free Chemistry Services
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We can visit your site for chemistry demos and seminars. Impress your colleagues and bring flow chemistry to your lab.
Phoenix Flow Reactor - High temperature and pressure reactor for novel heterocycle and compound synthesis (up to 450C)
H-Cube Pro and Gas Module - for gas reagent chemistry from hydrogenation to oxidation
H-Cube Midi – scale up H-Cube for 10-500g/day hydrogenations
IceCube - for low temperature and high energy reactions
Heather Graehl, MS, MBA Director of Sales North America
Based in sunny San Diego [email protected]
Onsite Demos & Seminars Available
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THANK YOU FOR YOUR ATTENTION!!
ANY QUESTIONS?