Process Optimization and Thermal Hazard Study for the Preparation of TBPB by a Two–Step Reaction
<p>Molecular structure of TBPB.</p> "> Figure 2
<p>Reaction equation for the two–step synthesis of TBPB.</p> "> Figure 3
<p>Surface diagram of three–dimensional response for the yield of TBPB.</p> "> Figure 4
<p>Desirability ramp for numerical optimization.</p> "> Figure 5
<p><span class="html-italic">T</span><sub>r</sub> change diagram of first reaction process.</p> "> Figure 6
<p><span class="html-italic">T</span><sub>r</sub> change diagram of second reaction process.</p> "> Figure 7
<p>Temperature and heat release rate curves in a calorimetric experiment of optimal condition’s first reaction process.</p> "> Figure 8
<p>Temperature and heat release rate curves in a calorimetric experiment of optimal condition’s second reaction process.</p> "> Figure 9
<p>Temperature and heat release rate curves in the calorimetric experiment of different process’s second reactions. (<b>a</b>) Process 1; (<b>b</b>) Process 2; (<b>c</b>) Process 3.</p> "> Figure 10
<p>Infrared characteristic peak for (<b>a</b>) H<sub>2</sub>O; (<b>b</b>) TBHP; (<b>c</b>) TBPB; (<b>d</b>) benzoyl chloride.</p> "> Figure 11
<p>The three–dimensional spectrum of absorbance–reaction time–light wavenumber. (<b>a</b>) First reaction process; (<b>b</b>) second reaction process.</p> "> Figure 12
<p>Temperature, heat release rate, and infrared characteristic peak change curves in the second reaction process.</p> "> Figure 13
<p>Plate microchannel reactor device and related instruments.</p> "> Figure 14
<p>The effect of temperature on reaction at different residence times.</p> "> Figure 15
<p>Temperature changes during the reaction process. (<b>a</b>) 0.75 min; (<b>b</b>) 1 min; (<b>c</b>) 2 min; (<b>d</b>) 3 min.</p> "> Figure 16
<p>Pressure changes during the reaction process.</p> "> Figure 17
<p>Working curves of standardized TBPB solution.</p> "> Figure 18
<p>GC of the oil phase.</p> "> Figure 19
<p>Heat flow curve.</p> "> Figure 20
<p>The temperature vs. time profile of the TBPB from TAC–500A.</p> "> Figure 21
<p>Geometry–optimized structure results. (<b>a</b>) TBHP; (<b>b</b>) NaOH; (<b>c</b>) sodium salt; (<b>d</b>) H<sub>2</sub>O; (<b>e</b>) TBPB; (<b>f</b>) NaCl; (<b>g</b>) benzoyl chloride.</p> "> Figure 22
<p>Reaction pathways and reaction enthalpy changes.</p> "> Figure 23
<p><math display="inline"><semantics> <mrow> <msub> <mrow> <mi mathvariant="normal">T</mi> </mrow> <mrow> <mi mathvariant="normal">c</mi> <mi mathvariant="normal">f</mi> </mrow> </msub> </mrow> </semantics></math> curves and <math display="inline"><semantics> <mrow> <mi mathvariant="normal">M</mi> <mi mathvariant="normal">T</mi> <mi mathvariant="normal">S</mi> <mi mathvariant="normal">R</mi> </mrow> </semantics></math> of optimal conditions of the first reaction process.</p> "> Figure 24
<p><math display="inline"><semantics> <mrow> <msub> <mrow> <mi mathvariant="normal">T</mi> </mrow> <mrow> <mi mathvariant="normal">c</mi> <mi mathvariant="normal">f</mi> </mrow> </msub> </mrow> </semantics></math> curves and <math display="inline"><semantics> <mrow> <mi mathvariant="normal">M</mi> <mi mathvariant="normal">T</mi> <mi mathvariant="normal">S</mi> <mi mathvariant="normal">R</mi> </mrow> </semantics></math>. (<b>a</b>) Optimal condition; (<b>b</b>) Process 1; (<b>c</b>) Process 2; (<b>d</b>) Process 3.</p> "> Figure 25
<p>The calculation results of <math display="inline"><semantics> <mrow> <msub> <mrow> <mi mathvariant="normal">T</mi> <mi mathvariant="normal">M</mi> <mi mathvariant="normal">R</mi> </mrow> <mrow> <mi mathvariant="normal">a</mi> <mi mathvariant="normal">d</mi> </mrow> </msub> </mrow> </semantics></math> vs. <math display="inline"><semantics> <mrow> <mi mathvariant="normal">T</mi> </mrow> </semantics></math> under adiabatic conditions of TBPB.</p> "> Figure 26
<p>Calculated m–ITHI value in the microchannel reactor.</p> "> Figure 27
<p>Calculated m–ITHI value in semi–batch mode.</p> ">
Abstract
:1. Introduction
2. Materials and Experimental
2.1. Reagents
2.2. Process Optimization
2.3. Reaction Calorimetry
2.4. Dynamic Scanning Calorimetry
2.5. Product Analysis
2.6. Reaction Monitoring Experiments
2.7. Adiabatic Experiment
2.8. Theoretical Calculation
2.9. Microchannel Experiment
3. Results and Discussion
3.1. Process Optimization and Exothermic Properties
3.1.1. Model Fitting
3.1.2. Effect of Different Factors on Responses
3.1.3. Optimal Process and Experiments
3.1.4. Exothermic Characterisation
3.2. Analysis of Exothermic Behavior of the Reaction
3.2.1. Calorimetric Experimental Results and Analyses
3.2.2. Exothermic Characterization of the Reaction Process
3.3. Continuous–Flow Process Studies
3.3.1. Effect of Temperature and Residence Time on the Reaction
3.3.2. Temperature and Pressure Variations in Microreactors
3.4. Gas Chromatography
3.5. DSC Results
3.6. ARC Results
3.7. Gaussian Simulation
3.8. Summary of Thermal Behavior Parameters
3.9. Process Heat Hazard Assessment
3.9.1. Risk Matrix Method
3.9.2. Stoessel Criticality Diagram
3.9.3. Quantitative Assessment of m–ITHI
4. Conclusions
- (1)
- The TBPB semi–intermittent synthesis process was optimized using Design–Expert software to analyze the exothermic properties, where an increase in NaOH concentration and a decrease in feeding time increased the reaction temperature. The optimum process conditions were temperature of 31.50 °C, feeding time of 22.00 min, and NaOH concentration of 15%. Based on the predictions of the model, the TBPB yield under these conditions was 84.06%, and the model was verified to have good accuracy through three experiments.
- (2)
- In the plate microchannel reaction process, the temperature and pressure changes in the reaction system can be monitored in real time using thermocouples and pressure sensors. When it was 50 °C and the residence time was 45 s, TBPB reached the highest yield of 83%.
- (3)
- The products were analyzed qualitatively and quantitatively by GC to obtain the peak times and working curves of TBPB, and the yield of the optimal process in EasyMax 102 was 88.93%. The exothermic properties were studied using RC1e to obtain values for the exothermic quantities of the reactions. The total heat release in the first step of the optimum process was 52.11 kJ and the total heat release in the second step of the optimum process was 253.45 kJ. The total heat release in Process 1 was 254.79 kJ, in Process 2 was 99.50 kJ, and in Process 3 was 182.23 kJ.
- (4)
- Real–time monitoring of the reactants and products during the reaction process using FTIR, combined with data from reaction calorimetry, revealed that the absorbance changes of the characteristic peaks of TBPB were consistent with the trend of the exothermic rate. In the second step of the TBPB half–gap synthesis process, the exotherm was mainly present in the TBPB generation phase after the start of feeding.
- (5)
- The thermal hazard assessment of the TBPB semi–intermittent synthesis process was carried out using the risk matrix method and the Stoessel criticality diagram method. Using the risk matrix methodology to obtain TMRad > 24, the hazard class for the second step of the TBPB semi–intermittent synthesis process involves acceptable risk, which is a low level of hazard and does not require special safety measures. Using the Stoessel criticality plot method, the overall thermal runaway hazard was assessed to be low when the reaction system was at 30 °C and below, both for the first– and second–step reactions. However, when the reaction temperature rose to 50 °C, the degree of thermal runaway of the reaction system rapidly rose to level 5. This is point with the highest degree of danger, as once cooling failure occurs, the temperature is out of control; it is very likely to cause accidents and must be optimized for the process. Finally, the reaction heat hazard in a continuous–flow microreactor as well as semi–batch mode was assessed using the cloud–model–based modified intrinsic thermal runaway hazard index (m–ITHI) method, and the m–ITHI values of the two reactors were compared. The m–ITHI value of 2.985 was obtained in the continuous–flow microreactor, which is classified as hazard class 1, and the m–ITHI value of 5.004 was obtained in semi–batch mode, which is classified as hazard class 2. The quantitative evaluation method suggests that the safety of a continuous–flow microreactor is higher than that of semi–batch mode, which provides some reference for the selection of high–risk and highly exothermic synthesis processes and reactors.
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Reagents | Molecular Formula | Purity (%) | Source |
---|---|---|---|
Tert–butyl hydroperoxide | C4H10O2 | 70 | Macklin |
Sodium hydroxide | NaOH | ≥99.0 | Sinopharm |
Sodium dodecyl benzene sulfonate | C18H29NaO3S | 95 | Aladdin |
Benzoyl chloride | C7H5ClO | 99 | Macklin |
Factors | Symbol | Level | ||
---|---|---|---|---|
−1 | 0 | 1 | ||
Reaction temperature (°C) | X1 | 10 | 30 | 50 |
Feeding time (min) | X2 | 10 | 20 | 30 |
NaOH concentration (%) | X3 | 5 | 10 | 15 |
Parameters | Conditions |
---|---|
Column | Capillary column |
Injector temperature | 75 °C |
Column temperature | 50 °C for 3.6 min and then raised to 120 °C for 9 min at 30 °C/min |
Detector temperature | 150 °C |
Injection volume | 1 μL |
Split ratio | 80:1 |
Run | Independent Variables | Dependent Variables | |||
---|---|---|---|---|---|
X1 | X2 | X3 | Y | ||
Exp. a | Pre. b | ||||
1 | 10 | 10 | 10 | 69.27 | 68.91 |
2 | 50 | 10 | 10 | 52.26 | 53.90 |
3 | 10 | 30 | 10 | 63.79 | 62.15 |
4 | 50 | 30 | 10 | 68.11 | 68.46 |
5 | 10 | 20 | 5 | 65.40 | 66.29 |
6 | 50 | 20 | 5 | 56.60 | 55.49 |
7 | 10 | 20 | 15 | 67.58 | 68.69 |
8 | 50 | 20 | 15 | 71.68 | 70.79 |
9 | 30 | 10 | 5 | 68.86 | 68.33 |
10 | 30 | 30 | 5 | 72.93 | 73.68 |
11 | 30 | 10 | 15 | 79.39 | 78.64 |
12 | 30 | 30 | 15 | 80.54 | 81.07 |
13 | 30 | 20 | 10 | 81.98 | 81.56 |
14 | 30 | 20 | 10 | 80.21 | 81.56 |
15 | 30 | 20 | 10 | 81.16 | 81.56 |
16 | 30 | 20 | 10 | 83.17 | 81.56 |
17 | 30 | 20 | 10 | 81.29 | 81.56 |
Factors and Responses | Objectives | Low Level (−1) | High Level (1) |
---|---|---|---|
—Reaction temperature (°C) | In range | 10 | 50 |
—Feeding time (min) | In range | 10 | 30 |
—NaOH concentration (%) | In range | 5 | 15 |
—TBPB yield (%) | Maximize | 52.26 | 100 |
TBPB Yield | |
---|---|
Process 1 | 87.27% |
Process 2 | 88.93% |
Process 3 | 88.43% |
Experimental mean | 88.21% |
Model predictions | 84.06% |
Relative error | 4.15% |
Parameter | Set Value |
---|---|
Flow velocity ratio | 1:3; 1:2 |
Oil bath temperature | 30 °C; 35 °C; 40 °C; 45 °C; 50 °C |
Residence time | 0.75 min; 1 min; 2 min; 3 min |
Chemicals | Sample Mass (mg) | Tonset (°C) | Tpeak (°C) | −∆Hd (J/g) |
---|---|---|---|---|
Benzoyl chloride | 6.32 | 200.56 | 205.90 | −176.02 |
TBHP | 5.93 | 100.40 | 101.30 | −371.00 |
Sample 1 | 6.78 | 113.63 | 113.64 | −975.38 |
TBPB | 5.44 | 129.44 | 154.91 | 709.70 |
Reaction | ΔHr/kJ | Cp/J (K−1·g−1) | M/g | Y/% | ΔTad/K | ΔTad,r/K |
---|---|---|---|---|---|---|
Optimal process | 52.1 | 4.79 | 786.14 | / | 13.84 | / |
Reaction | ΔHr/kJ | Cp/J (K−1·g−1) | M/g | Y/% | ΔTad/K | ΔTad,r/K |
---|---|---|---|---|---|---|
Optimal process | 253.45 | 2.23 | 1056.74 | 97.91 | 107.55 | 109.85 |
Process 1 | 254.79 | 2.21 | 1056.74 | 88.10 | 109.10 | 123.84 |
Process 2 | 99.50 | 3.24 | 1166.10 | 87.33 | 26.34 | 30.16 |
Process 3 | 182.23 | 3.39 | 1193.52 | 94.27 | 45.04 | 47.78 |
Reaction | Tp |
---|---|
Optimal process first–step reaction | 30.00 °C |
Optimal process second–step reaction | 31.50 °C |
Process 1 s step reaction | 50.00 °C |
Process 2 s step reaction | 10.00 °C |
Process 3 s step reaction | 10.00 °C |
Sample | ΔTad,r/K | Severity | TMRad/h | Possibility | Risk Level | Thermal Hazard |
---|---|---|---|---|---|---|
TBPB | 109.85 | medium | >24 | hardly | 1 | acceptable |
Reaction | Tp/°C | MTSR/°C | MTT/°C | TD24/°C | Class |
---|---|---|---|---|---|
Optimal process | 30.00 | 31.45 | 100.00 | >350 | 1 |
Reaction | Tp/°C | MTSR, r/°C | MTT/°C | TD24/°C | Class |
---|---|---|---|---|---|
Optimal process | 31.50 | 54.26 | 100.00 | 70.60 | 2 |
Process 1 | 50.00 | 89.47 | 100.00 | 70.60 | 5 |
Process 2 | 10.00 | 21.80 | 100.00 | 70.60 | 2 |
Process 3 | 10.00 | 46.20 | 100.00 | 70.60 | 2 |
Parameter | Microchannel Reactor | RC1e |
---|---|---|
Total volume of reaction (mL) | 23.00 | 975.00 |
Stay time (min) | 0.75 | 60.00 |
Yield (%) | 83.00 | 97.91 |
Spatiotemporal yield (g·L−1·s−1) | 0.58 | 0.07 |
Annual output (t/unit) | 0.39 | 1.83 |
Total material quantity (kg) | 484.00 | 4050.00 |
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Wang, Y.-Y.; Zhang, D.-F.; Zhang, H.-R.; Liu, W.-J.; Chen, Z.-Q.; Jiang, J.-C.; Ni, L. Process Optimization and Thermal Hazard Study for the Preparation of TBPB by a Two–Step Reaction. Sustainability 2024, 16, 8568. https://doi.org/10.3390/su16198568
Wang Y-Y, Zhang D-F, Zhang H-R, Liu W-J, Chen Z-Q, Jiang J-C, Ni L. Process Optimization and Thermal Hazard Study for the Preparation of TBPB by a Two–Step Reaction. Sustainability. 2024; 16(19):8568. https://doi.org/10.3390/su16198568
Chicago/Turabian StyleWang, Yuan-Yuan, Dan-Feng Zhang, Hong-Rui Zhang, Wen-Jun Liu, Zhi-Quan Chen, Jun-Cheng Jiang, and Lei Ni. 2024. "Process Optimization and Thermal Hazard Study for the Preparation of TBPB by a Two–Step Reaction" Sustainability 16, no. 19: 8568. https://doi.org/10.3390/su16198568