Workshop I: Automated Data Preparation and Spectral Modeling
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1 qnmr-summit 217 Workshop I: Automated Data Preparation and Spectral Modeling Simon Kern, Klas Meyer, Svetlana Guhl, Patrick Gräßer, Lukas Wander, Andrea Paul, Michael Maiwald Bundesanstalt für Materialforschung und -prüfung (BAM) Division 1.4 Process Analytical Technology Richard-Willstätter-Str. 11 D Berlin, Germany This project has received funding from the European Union s Horizon 22 research and innovation programme under grant agreement N
2 CONSENS: Case Study 1 Intensified Synthesis of Organic Compounds Modular plant Control Data-usage Sensors Model-based control Online state & parameter estimation Online performance monitoring Sensor failure detection & correction Other sensors Other Sensor Source: INVITE GmbH Explosion proof housing NMR By-pass stream FNB Aniline Dos. Dos. Mixing, cooling LiHMDS Dos. Product stream Reaction Scheme: S. Kern Automated Data Preparation and Spectral Modeling 2
3 Online 1H NMR Spectra of Lithiation Reaction Step High field (5 MHz) Low field (43 MHz) start of reaction end of reaction start of reaction end of reaction intensity, I / a.u. intensity, I / a.u aromats 1 solvent 15 HMDS aromats intensity, I / a.u. intensity, I / a.u start of reaction end of reaction 1 start of reaction end of reaction 12 5 chemical shift, δ / ppm chemical shift, δ / ppm chemical shift, δ / ppm S. Kern Automated Data Preparation and Spectral Modeling chemical shift, δ / ppm 3
4 Data Processing for Low-field NMR in Matlab Raw spectra single scan each 15s in flow Phase correction Baseline correction Alignment S. Kern Automated Data Preparation and Spectral Modeling 4
5 Data Processing for Low-field NMR in Matlab Raw spectra Phase correction Entropy minimization method: Chen et al., J Magn Reson. 22, 158, Baseline correction Alignment S. Kern Automated Data Preparation and Spectral Modeling 5
6 Data Processing for Low-field NMR in Matlab Raw spectra Phase correction Low-order Polynomial fit: Mazet et al., Chemometrics Intell. Lab. Sys. 25, 76, Baseline correction Alignment S. Kern Automated Data Preparation and Spectral Modeling 6
7 Data Processing for Low-field NMR in Matlab Raw spectra Phase correction Alignment to reference signal (THF) using icoshift: Savorani et al., J Magn Reson. 21, 2, Baseline correction Alignment S. Kern Automated Data Preparation and Spectral Modeling 7
8 Residuals Intensity Spectral Modeling Modeling Analysis peak fitting of pure component spectra mixture model component fitting calculation of component area Group of peaks represent pure component spectra 12 Spectral model for pure component 1 8 Hard Model Spectrum (NDPA) 6 Pseudo-Voigt function 4 V = α β exp ln 2 2 x δ γ β γ 2 x δ 2 γ 2 2 α = peak maximum β = Gaussian-Lorentzian-ratio γ = half width δ = center position ppm S. Kern Automated Data Preparation and Spectral Modeling 8
9 IHM component fitting Pure component models Modeling Mixture model No. components 3 Experimental Spectrum Peaks per component Degree of freedom (total free parameters) 22, 21, Considered interacting peaks 25 Max. peak shift.1 ppm Peak area ratio for each pure component model is kept constant! S. Kern Automated Data Preparation and Spectral Modeling 9
10 IHM component fitting Pure component models Analysis component fitting Deconvoluted spectrum Experimental Spectrum S. Kern Automated Data Preparation and Spectral Modeling 1
11 Results: Reaction Characterization Lab Experiments in Batch along Reaction Co-ordinate 3 semi-batch reaction with variing starting concentrations Classification of steady states 15 Spectra for each HF- and NF-NMR deviation of.3 mol/l Bad shim Reaction Scheme: S. Kern Automated Data Preparation and Spectral Modeling 11
12 Smart NMR Sensor Concept S. Kern Low field NMR spectroscopy for sustainable and flexible production 12
13 NMR Group at BAM THANK YOU! Jürgen Kolz Magritek Harald Pape PTB Ullrich Koch Magritek Clemens Minnich S-Pact Juan Perlo Magritek Dirk Engel S-Pact Mike Bernstein MestreLab Alfons Steil PSG Petro Service CONSENS Integrated Control and Sensing for Sustainable Operation of Flexible Intensified Processes, funded by the European Union s Horizon 22 research and innovation programme under grant agreement N THIS DOCUMENT IS PROVIDED "AS IS" WITH NO WARRANTIES WHATSOEVER, INCLUDING ANY WARRANTY OF MERCHANTABILITY, NONINFRINGEMENT, FITNESS FOR ANY PARTICULAR PURPOSE, OR ANY WARRANTY OTHERWISE ARISING OUT OF ANY PROPOSAL, SPECIFICATION OR SAMPLE. Any liability, including liability for infringement of any proprietary rights, relating to use of information in this document is disclaimed. No license, express or implied, by estoppels or otherwise, to any intellectual property rights are granted herein. The members of the project CONSENS do not accept any liability for actions or omissions of CONSENS members or third parties and disclaims any obligation to enforce the use of this document. This document is subject to change without notice.
14 CONSENS: Smart Online NMR Sensor for Advanced Process Control Flexible Intensified Continuous Plant Characteristics Miniaturized equipment Benefits Product uniformity Intensified heat & mass transfer Sustainability Fast adaption to market demand Possibly modular setup Innovative products Containerized modular plant Source: INVITE GmbH S. Kern Low field NMR spectroscopy for sustainable and flexible production 14
15 Industrial Automation Current Technical and Cultural Requirements to Process Sensors Sensor Explosion safety Communication Full Documentation Safety and Operation Fully functional instrument Automation Robustness Applied standards (e.g. EN 679) Zone classification Explosion group Temperature class Safeguard control SIL = safety integrity level 4 2 ma signals Fast field bus (e.g., remote control) ATEX certificate CE certificate (Europe) Documentation (Manual) Safety audits Safety instructions Operation training Pressurized housing Status signals Leakage control S. Kern Low field NMR spectroscopy for sustainable and flexible production 15
16 Communication Concept Safeguard control - Leakage, T, p NAMUR status signals Conventional 4-2 ma OPC-UA Client Fast field bus S. Kern Low field NMR spectroscopy for sustainable and flexible production 16
17 (2) Validation Lab Experiments in Tube Reactor Continuous Lithiation Reaction Set-up at BAM Two series covering 1 : 1 : 2.3 (FNB : Aniline : Li-HMDS) Additional experiments, e.g., concentration variation in THF etc S. Kern Low field NMR spectroscopy for sustainable and flexible production 17
18 Monitoring of Continuous Aromatic Substitution Reaction by Low Field NMR Lunch time R = H, CH 3, F Various substituents Fast adaption of spectral models to various substituents Calibration-free S. Kern Low field NMR spectroscopy for sustainable and flexible production 18
19 Reaction Characterization in Lab Lab Experiments in Batch along Reaction Co-ordinate Data in parallel acquired with high-field and low-field spectrometer Fast and slow loop Li-HMDS was dosed stepwise Experimental set-up Li-HMDS P1 Low-field NF- NMR P2 4 mm ( ID) F1 V1 V3 V2 PI 1 PI 2 High-field HF-NMR NMR 1 mm ( ID) 2.5 ml/min.4 ml/min FIC Exothermic reaction required cooling (28.5 C) Li-HMDS in two-fold excess Reaction Scheme: heating and cooling Aniline + FNB C S. Kern Low field NMR spectroscopy for sustainable and flexible production 19
20 E(t) / min F(t) pump rate norm. 1 H-Integral CHCl 3, I / a.u. -1 E (t) / min F(t) -1 Validation of Lab Experiments in Tube Reactor Continuous Lithiation Reaction Set-up at BAM Low-field NMR High-field NMR FNB Aniline Dos. Dos. Mixing LiHMDS Dos. 2 E( t) F( t) LF-NMR 2 1/8ꞌꞌ tube reactor 1.5 t 1.5 Step tracer experiments Step 1 Step 2 St ep 3 S tep 4 3:27 3:2 3:1 3:23 8:55 8:49 8:35 9:9 - LF, t / min - HF, t / min pump rate LF-NMR HF-NMR 1 2 E( t) F( t) HF-NMR :: :1: :2: :3: :4: :5: 1:: 1:1: Time, t / hh:mm:ss S. Kern Low field NMR spectroscopy for sustainable and flexible production Time, t / min 2
21 Experimental Design Continuous Lithiation Reaction Set-up at BAM Reaction Scheme: Independent variation of flowrates / stoichiometric conditions Coarse variation: Fine variation: Optimal process window S. Kern Low field NMR spectroscopy for sustainable and flexible production 21
22 NF-NMR Co n c entration, c / mol L -1 Monitoring of Continuous Aromatic Substitution Reaction by Low Field NMR Toluidin FNB Li-Toluidin Li-MNDPA HF-NMR Concentration, c / mol L S. Kern Low field NMR spectroscopy for sustainable and flexible production 22
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