Optimization of a hazardous reaction with strong gas release - ReactIR in solution and gas phase -
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1 Real Time Analytics User s Forum 24 Optimization of a hazardous reaction with strong gas release - ReactIR in solution and gas phase - Kai Lovis Schering AG
2 Content Introduction Initial situation / Problems / Risks First experiments in solution Usage of the new gas cell for ReactIR Kinetic calculations / Reaction mechanism Summary
3 Introduction Overview of reaction HCOOH Cl-SO 2 -N C O Cl-SO 2 -NH 2 CH 2 Cl 2 + HO H 2 N R O chloro sulfonylisocyanate sulfamoylchloride Only the synthesis of the sulfamoyl chloride (1 st step) is critical
4 Supposed mechanism of the 1 st reaction step Initial Situation Cl-SO 2 -N C O Cl-SO 2 -NH 2 Chlorosulfonylisocyanate HCOOH Cl-SO 2 N H O O O intermediate IM H -CO,-CO 2 Sulfamoyl chloride yield quantitative high purity but: a lot of gas!! Previous assumptions of the reaction: fast formation of intermediate IM delayed cleavage of CO 2 and CO possibility of uncontrolled accumulation of IM risk of spontaneous release of the whole gas volume (Runaway) (approx. 7 m 3 gas in 25 L-vessel!) rigorous safety requirements for the manufacturing process
5 Hazard analysis in safety lab Initial Situation Conditions: Recipe based on optimization results Dosage of HCOOH over 1 h (Reflux) Dosage period of HCOOH gas volume [cm 3 ] IT [ C] bservations: delayed and apparently spontaneous gas release Runaway! Volume [ml] gas flow [cm 3 /h] T [ C] onsequences for the 1 st campaign: slow, batchwise dosage of HCOOH long breaks before dosage of next portion t [h]
6 First Experiments eproducing the manufacturing procedure at lab: conditions: charge of the total mass of CSI dosage of HCOOH in 8 portions duration of each dosage-phase: 2 min volumetric measurement of the gas (sum of CO 2 /CO) IR-signal IR-Signal Gasfreisetzung release [ml/min] product SMC (amine) HCOOH Dosierung dosage observations: partly delayed gas release at the outset strong subsequent release of gas at the outset nearly dosagecontrolled gas release at high conversions t/min
7 ReactIR-Study in liquid phase (I) Simultaneous, fast addition of isocyanate und HCOOH (in 5 portions): 3D-series of IR-spectra in liquid phase (DiComp-probe) Solvent CH 2 Cl 2 is subtracted Isocyanat (-N=C=O) HCOOH (-C=O) Amidn (-NH 2 ) IM 1 (-C=O) IM 2
8 ReactIR-Study in liquid phase (II) Simultaneous, fast addition of CSI und HCOOH (in 5 portions): blue: start spectrum red: end spectrum Resulting concentration profiles: -N=C=O diamond (probe) IM 2 IM 1 anhydride HCOOH product (amine) IR-Signal N=C=O CSI amine SMC HCOOH IM1 IM2 Gas high increase of reaction rate by autocatalysis appearance of 2 intermediates: IM 1 corresponds to anhydride IM 1-kinetic like isocyanate or HCOOH IM 2 is formed after delay (IR-bands can not be assigned) t Zeit/min [min]
9 Use of the ReactIR Gas Cell (I) Gas cell for ReactIR: qualitative and quantitative analysis of gas mixtures general information: diagram: IR-beam (from / to spektrometer) IR-window (ZnSe) Gas volume (optical path-length 2 x 5 cm) Gas mixture (from reactor) mirror (gold) suitable for: all compounds in gas phase (including solvents) except linear homonuclear (e.g. He, O 2, N 2, H 2, Cl 2 ) pressure: 1 mbar - 1 bar used at Schering for: CO/CO 2 CSI reaction ozone H 2 O/EtOH monitoring of an ozonolysis drying of a drug substance
10 Use of the ReactIR Gas Cell (II) ReactIR with gas cell RC 1
11 Use of the ReactIR Gas Cell (III) Parts from IR-spectra of the gas phase during the CSI reaction CO 2 CO CO 2 CO 2 υ sym cm -1 CH 2 Cl 2 HCl υ Asym cm -1 R-branch S-branch Q-branch excellent separation of the IR-bands in gas phase even rotational fine structure of CO can be recognized
12 Use of the ReactIR Gas Cell (IV) Simultaneous, fast addition of CSI und HCOOH (5 portions): 3D-series of IR-spectra in gas phase: resulting profiles: CO 2 CO Absorptionseinheiten CO2 CO gas Gas overall gesamt increase of reaction rate delayed release of CO 2 compared with CO Zeit t [min] decarbonylation takes place before decarboxylation!!
13 Use of the ReactIR Gas Cell (Ozonolysis) Calibration of an ozone generator at CChD ozone-signal at varied oxygen stream: n 3 (142 cm -1 ).2.15 Ozon-Anteil Ozone fraction Ozone Ozon-Anteil fraction Oxygen Sauerstoffstrom flow [L/h](L/h) quantitative calibration of spectra: 1. with known molarabsorptivity (literature) 2. by titration
14 Use of the ReactIR Gas Cell (V) Rerun of the Standard Operation Procedure with gas cell: Profiles of released gas phase (by IR-spectroscopy) 5 Flowgesamt overall [ml/min] FlowCO2 [ml/min] Gasflow [ml/min] FlowCO [ml/min] black: Sum of CO + CO 2 red: CO blue: CO Zeit t [min] Sum of CO 2 and CO corresponds to previous results Decarbonylation (CO) is nearly dosage-controlled Decarboxylation (CO 2 ) increases (autocatalysis) A safety risk is only presented by CO 2 (half of the total gas volume)
15 Resulting reaction mechanism based on ReactIR-data : Reaction Mechanism O R O O N=C=O R R k 1 k 2 NH2 R NH OH k 3 + NH O H O CSI anhydride carbamid acid Sulfamoyl chloride OH 1. Resulting rate laws/-constants: k 1: autocatalyzed => k1 = f (conversion) k 2: much higher than k1 and k3 => k2 > k1, k3 k 3: strongly autocatalyzed => k3 = f (conversion) (acid- or base catalysis) 2. Determination of kinetic constants by software PRESTO: fitting the parameters to lab experiments C + + O O C O
16 Simulation of Standard Operation Procedure: dosage of HCOOH (5 x) to charged CSI kinetic calculations with PRESTO Verification of the kinetic model Simulation of the safety lab batch: continuous dosage of HCOOH (1 h) to CSI Signale CO2/CO CO2 (berechnet) CO2 (gemessen) CO (berechnet) CO (gemessen) dosage phase Signale CO2/CO CO2 (berechnet) CO (berechnet) dosage phase Zeit [min] t [min] profiles of released gas components correspond closely to calculations t Zeit [min] [min] simulation shows good agreement with safety lab Runaway no uncontrolled gas release, but calculable, autocatalyzed release of CO 2
17 Kinetic calculations Result of a PRESTO-simulation: all components were added quickly and simultaneously Set up: definition of real system (workshop): reactor (size, semibatch,...) gas cell reaction components (e.g. concentrations) operating mode recipe (Additiontime, -duration, -amount) reaction steps Parameters: k1 = 1.1e-3 L/(mol s) + autokatalysis-term k2 = 1.5e-2 L/(mol s) k3 = 3.e-3 L/(mol s) + autokatalysis-term
18 Optimization Experiments Rerun of the safty lab experiment by using ReactIR gas cell Dosage of HCOOH in 1 h at 5 C (IT)
19 Specific Optimization of Dosage-controlled Gas Release Situation after optimization: Flow CO2 [ml/min] Flow CO [ml/min] Gasvolumen gesamt [ml] 6 45 Gasfluß [ml/min] 8 3 Gasvolumen/[mL] t/min dosage-controlled CO 2 -release!! dosage breaks are not necessary!!
20 Optimization of sulfamoyl chloride formation achieved by using ReactIR: specific kinetic experiments in solution with DiComp-Probe Summary final determination of the reaction mechanism by IR-measurements in gas phase with ReactIR-Gas cell Specific search for new process variations was possible Simulation of process variations using softwaretool PRESTO
21 Who did the job? Christian Finke Monika Linnenlücke Kai Lovis
22 Ozonolysis Messung 117_4 Ozon MeCl 1 1 Ozon im Abgas/ % Ozon im Abgas/ % Ozon-Zugabe /g Absorbiertes Ozon im Reaktor [g/h] Absorbiertes Ozon im Reaktor [g/h] Zeit/min
23 gas flow + heat flow Wärmeleistung + Gasfluss 8 2 Gasstrom Leistung in Watt/kgERM 4 2 CO 2 CO 5-5 Gasfluss in l/mol/h Wärmestrom Dosierung Zeit in s
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