A Continuous Flow Microwave Reactor for Conducting. High Temperature and High Pressure Chemical Reactions
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1 A Continuous Flow Microwave Reactor for Conducting High Temperature and High Pressure Chemical Reactions Supporting Information Jennifer M. Sauks, 1,2 Debasis Mallik, 2 Yuri Lawryshyn, 1 Timothy P. Bender, 1 and Michael G. Organ 1,2 * [1] Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College St., Toronto, Ontario, Canada M5S 3E5 [2] Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, Canada, M3J 1Phemistry Department, York University Fax: (+1) organ@yorku.ca S1
2 Table of Contents Figure S1. Photograph of Biotage Initiator Microwave that has been modified to accommodate a reactor tube that flows from the top to the bottom of the waveguide...s3 Figure S2. Close-up photograph of SiC tube through the viewing window (see Fig. 1) that traverses the waveguide of Biotage Initiator Synthesizer that is heating as a consequence of being irradiated by microwave irradiation.. S3 Figure S3. Cross sectional schematic of the pressure-creating device.s4 Figure S4. Full schematic of high temperature/high pressure flow synthesis reactor including inline GCMS analysis...s5 Figure S5. Photograph of high temperature/high pressure flow synthesis reactor including in-line GCMS analysis..s6 S7 Table S1 Detailed standard operating procedure for high temperature/high pressure reactor described in manuscript, working with two syringe pumps and the option to use in-line analytics... S8 Table S2 Detailed standard operating procedure to prime the high temperature/high pressure reactor described in manuscript...s9 Table S3 Detailed standard operating procedure to perform a chemical transformation in the high temperature/high pressure reactor described in manuscript...s10 Table S4. Detailed standard operating procedure to perform in-line analysis by GCMS of an ongoing transformation in the high temperature/high pressure reactor described in manuscript S11 Synthetic Procedures.S12 2-Allylphenol...S12 2-Methylbenzimidazole...S12 References... S12 S2
3 Figure S1. Photograph of Biotage Initiator Microwave that has been modified to accommodate a reactor tube that flows from the top to the bottom of the waveguide. Figure S2. Close-up photograph of SiC tube through the viewing window (see Fig. 1) that traverses the waveguide of Biotage Initiator Synthesizer that is heating as a consequence of being irradiated by microwave irradiation. S3
4 Figure S3. Cross sectional schematic of the pressure-creating device. S4
5 Figure S4. Full schematic of high temperature/high pressure flow synthesis reactor including inline GCMS analysis. S5
6 Figure S5. Photograph of high temperature/high pressure flow synthesis reactor including in-line GCMS analysis. a) b) S6
7 c) a) Photograph of entire reactor set up from reagent delivery (high-pressure pumps) to analysis (GCMS). b) Blow up of pressure-creating device and 4-way valve that sends product stream to collection and to in-line analysis. c) Blow up of custom-built flow cell. Syringe needle of robot enters the sampling port and delivers samples to robot for work up, dilution, and injection into GCMS. S7
8 Table S1 Detailed standard operating procedure for high temperature/high pressure reactor described in manuscript, working with two syringe pumps and the option to use in-line analytics. Note: Start with all valves opened, however, if the clean sequence occurs right after a reaction has been completed, keep V-1 and V-2 closed to preserve the nitrogen gas in PB- 1. Turn on all process equipment. The pumps will start in opposite positions, so P-1 is set to infuse (meaning the syringe is empty but ready to infuse) and P-2 is set to refill. Step Operation Notes 1 Fill reservoir R-1 and R-2 with pure solvent. Pure solvent is the solvent used in the reaction. 2 Close V-1, V-2 and V-3. Set RV-1 to position 1-4, 2-3. Close V-1 and V-2 if they are not already closed. 3 Set V-4 open to P-2, set V-5 open to R-1, and set V-7 open to R-2. 4 Start pump program. P-1 starts with infuse mode, P-2 starts with refill mode to 2 ml endpoint. 5 Set V-7 to RT-1. 6 P-1 set to refill mode and P-2 set to infuse to 2 ml endpoint. Collect reactor effluent in waste W-1. 7 Set V-4 to P-1, set V-5 to RT-1 and set V-7 to R-2. 8 P-1 set to infuse mode and P-2 set to refill to 2 ml endpoint. Collect reactor effluent in waste W-1. Automated by pump program. P-2 cleaning the reactor. Automated by pump program. P-1 cleaning the reactor. 9 Set V-4 open to P-2, set V-5 open to R-1, and set V-7 open to RT Repeat steps 6 9 twenty five times. This is equal to 50 ml of cleaning per pump. 11 Remove R-1 and R-2 and repeat steps 6 9 four times using air, and keeping V-6 open for the duration of the steps. This sequence helps to clear out all solvent from the process lines. After cleaning, valves are in the following positions: Closed: V-1, V-2, V-3 // Open: V-4 (open to P-2), V-5 (open to R-1), V-6, V-7 (open to RT-1), V-8 (open to R-3), V-9, V-10, V-11, RV-1 (at position 1-4, 2-3) S8
9 Table S2 Detailed standard operating procedure to prime the high temperature/high pressure reactor described in manuscript. Note: All valves start in same position when cleaning finished. The pumps will start in opposite positions, so P-1 is set to infuse (meaning the syringe is empty but ready to infuse) and P-2 is set to refill. Step Operation Notes 1 Fill reservoir R-1 and R-2 with reactants. 2 Open V-1 and regulate nitrogen gas cylinder to fill PB-1 to 50 psi above desired operating pressure using PR-1. 3 Close V-1. 4 Set V-7 open to R-2. 5 Start pump program. P-1 starts with infuse mode, P-2 starts with refill mode to 2 ml endpoint. 6 P-1 set to refill mode and P-2 set to infuse to 2 ml endpoint. 7 P-1 set to infuse mode, P-2 set to refill mode to 2 ml endpoint. 8 Set V-7 to RT-1. 9 P-1 set to refill mode and P-2 set to infuse to 2 ml endpoint. 10 Set V-4 open to P-1, set V-5 to RT-1, and set V-7 to R P-1 set to infuse mode and P-2 set to refill to 2 Charges PB-1 with nitrogen gas to the desired operating pressure. Automated by pump program. This sequence removes bubbles from the reactants in the pumps. Automated by pump program. This sequence removes bubbles from the reactants in the pumps. Automated by pump program. P-2 priming the reactor. Automated by pump program. P-1 priming the reactor. ml endpoint. Collect prime overflow in W Set V-4 open to P-2, set V-5 open to R-1, and set V-7 open to RT Repeat steps 9 12 two times. This is equal to 2 x 2 ml of priming per pump. 14 Close V-6. Open V-2. Pressurizes reactor. After priming, valves are in the following positions: Closed: V-1, V-3, V-6 // Open: V-2, V-4 (open to P-2), V-5 (open to R-1), V-7 (open to RT-1), V-8 (open to R-3), V-9, V-10, V-11, RV-1 (at position 1-4, 2-3) P-1 is in position to be refill, while P-2 is full and ready to infuse reactants into the reactor. S9
10 Table S3 Detailed standard operating procedure to perform a chemical transformation in the high temperature/high pressure reactor described in manuscript. Note: All valves in same position when priming finished. Step Operation Notes 1 Set MW-1 to power rating that will achieve desired temperature. 2 Monitor reactor with IR camera to determine when the tube is at desired operating temperature. Throughout the reaction, monitor tube surface temperature with IR camera and adjust MW-1 power settings as appropriate. 3 P-1 set to refill mode and P-2 set to infuse to 2 ml endpoint. 4 Set V-4 open to P-1, set V-5 to RT-1, and set V-7 to R-2. 5 P-1 set to infuse mode and P-2 set to refill to 2 ml endpoint. 6 Set V-4 open to P-2, set V-5 open to R-1, and set V-7 open to RT-1. 7 Repeat steps 3-6 for as many times as required to pump entire reaction mixture through the reactor. Once at desired temperature, proceed to step 3. Automated by pump program. P- 2 pumps reactants into the reactor. Automated by pump program. P- 1 pumps reactants into the reactor. Each time steps 3 6 are repeated, 4 ml of reactants have been pumped into the reactor. 8 To take a sample using the in-line analytics, see In-Line Analytic Sequence below. Otherwise, proceed to step 9 to end reaction sequence. 9 Close V-2. Turn off MW-1 and stop pump program. 10 Allow ten minutes for cooling. 11 Slowly open V-3. Vents the nitrogen gas from the reactor to the fume hood. 12 Open V-6. Allow products to drain from the reactor into C After collection, proceed to Clean Sequence to clean out the reactor. S10
11 Table S4. Detailed standard operating procedure to perform in-line analysis by GCMS of an ongoing transformation in the high temperature/high pressure reactor described in manuscript. Step Operation Notes 1 Close V-9, V-10, and set RV-1 to position 1-2, Fill R-3 with pure solvent. Same solvent that is used in the reaction. 3 Set P-3 to refill to 30 ml endpoint from R-3. 4 Set V-8 to RV-1. 5 Set P-3 to infuse to 5 ml endpoint. Collect overflow of prime in W-1. 6 Open V-6. Wait 10 seconds. 7 Close V-6. 8 Open V-10, set RV-1 to position 2-3, 1-4, and set P-3 to infuse to 2 ml endpoint. Start CombiPAL to take injection. 9 After CombiPAL has taken an injection from the flow cell, open V-9 and set P-3 to infuse to 20 ml endpoint. Collect cleaning solution in W Set V-8 to R-3. Set P-3 to refill to 30 ml endpoint. 11 Close V-9. Set V-8 to RV-1. Set P-3 to infuse to 30 ml endpoint. Collect cleaning solution in W Set V-8 to R-3. Set P-3 to refill to 10 ml endpoint. 13 Set V-8 to RV-1. Set P-3 to infuse to 10 ml endpoint. Collect cleaning solution in W Start CombiPAL to take solvent injection from flow cell. 15 Remove R-3. Set V-8 to the atmosphere. Set P-3 to refill to 30 ml endpoint. 16 Set V-8 to RV-1. Set P-3 to infuse to 30 ml endpoint. Collect cleaning solution in W-2. Primes process lines from P-3 to RV-1. Flowrate: 5 ml/min Sample taken from flow cell by CombiPAL. Sequence to start cleaning the inline analytics. Flowrate: 25 ml/min. Sequence to continue cleaning the in-line analytics. Flowrate: 25 ml/min. Final sequence to continue cleaning the in-line analytics. Flowrate: 25 ml/min. Sample taken from flow cell by CombiPAL. This ensures that the system is clean before the next sample. Removes all solvent in the process lines using air pumped through the system. Flowrate: 25 ml/min. S11
12 Synthetic Procedures: Starting materials and solvents were obtained from commercial suppliers and were used without further purification. 1 H NMR spectra were recorded from a Bruker 300 MHz AV spectrometer. All experiments listed below were carried out using reactor configuration shown in Figure S5 following the standard operating procedures (SOP) described in Tables S1-S4. 2-Allylphenol: A 10 ml solution of allyl phenyl ether (6.71 g) in toluene was prepared. The reactor was initially primed with toluene before being pressurized to 580 psi. The 2.5 ml syringe pump was filled with reactants to the 2 ml mark, and the microwave was powered up to 95 W initially to get the average surface temperature to 260 C, as indicated by the external IR camera. Once at steady state temperature, the pump was turned on to a flow rate of 25 L/min. Over the course of the reaction, the average surface temperature was monitored and the power setting on the microwave adjusted as necessary to maintain 260 C. After the reactants had completely infused, the pump was refilled with 2 ml of pure toluene, which was infused into the reactor at the same reaction conditions in order to flush the lines and completely irradiate all of the reactants. At the completion of the flush, the microwave was turned off, all valves were closed and the reactor was allowed to cool for 10 minutes before venting the pressure through the vent valve V-3. The product valve V-6 was opened to collect the product/solvent mixture (a yellow oil). The crude mixture was taken without further workup or purification for analysis by 1 H NMR spectroscopy at 300 MHz in CDCl 3. The spectral data for 2-allylphenol were consistent with that in the literature. 1 2-Methylbenzimidazole: A 10 ml solution of g of o-phenylendiamine in acetic acid was prepared. The reactor was initially primed with acetic acid before being pressurized to 650 psi pressure. The 2.5 ml syringe pump was filled with reactants to the 2 ml mark. The microwave was powered up to 50 W initially and was reduced to 48 W over the course of the reaction in order to achieve an average surface temperature of 170 C, as indicated by the IR camera. Once at steady state temperature, the pump was turned on to a flow rate of 200 L/min. Over the course of the reaction, the average surface temperature was monitored and the power setting on the microwave adjusted as necessary to maintain 170 C. After the reactants had completely infused, the pump was refilled with 2 ml of pure acetic acid, which was infused into the reactor at the same reaction conditions in order to flush the lines and completely irradiate all of the reactants. At the completion of the flush, the microwave was turned off, all valves were closed and the reactor was allowed to cool for 10 minutes before venting pressure through vent valve V-3. The product valve V-6 was opened to collect the product/solvent mixture (a yellow oil). The crude mixture was taken without further workup or purification for analysis by 1 H NMR spectroscopy at 300 MHz in DMSO-d 6. The spectral data for 2-methylbenzimidazole were consistent with that in the literature. 1 References: [1] Spectra for analytically-pure samples were obtained from Sigma-Aldrich Inc. S12
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