One-Pot Conversion of Methane to Light Olefins or Higher Hydrocarbons through H-SAPO-34 Catalyzed in-situ Halogenation
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1 S1 Supporting Information One-Pot Conversion of Methane to Light Olefins or Higher Hydrocarbons through H-SAPO-34 Catalyzed in-situ Halogenation Patrice T. D. Batamack, Thomas Mathew, G. K. Surya Prakash* Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA , USA. Table of Contents Content Page 1. Experimental S2 a. Materials S2 b. Catalytic tests S2 c. Procedures Gas chromatograms and NMR spectra of methane chlorination and bromination over H-SAPO-34 S3 d. List of Figures S4 2. Schemes S5 3. Tables S6 4. Figures S7 5. Additional Figures: GC and NMR Spectra S10 6. References S32
2 S2 Experimental Materials Materials: H-SAPO-34 (Al+P / Si = 5.57) was generously provided by UOP in the powder form. The preparation of the catalyst is described in reference 4. The synthesis formulation of the catalyst in molar basis was 1.0 DPA / 0.5 TEAOH / 0.1 SiO 2 Al 2 O 3 P 2 O 5 with a crystallization time of 17 h at 448 K (DPA: di-n-propylamine; TEAOH: Tetraethylammonium hydroxide). The chemical composition of catalyst was (Si 0.14 Al 0.55 P 0.30 ) O 2 with 50% of the particles smaller than 1.2 µm. The acid density of 1.38 acid site per cage was determined by NH 3 -TPD adsorption. The surface area, 438 m 2 /g, of the catalyst degassed at 673 K for 12 h was measured using NOVA 2200e Surface Area and Pore Size Analyzer; the pore diameter 37.2 Å and the pore volume 0.20 cc/g. Bromine (99.5+ %) was purchased from Sigma-Aldrich and Chlorine (99.5+ %) from Gilmore. Methane (ultra-high purity) was obtained from Airgas; nitrogen (pre-purified grade) and oxygen from Gilmore. Catalytic Tests Experiments were performed using a vertical 9 mm OD quartz tubular reactor and 620 mm length. In a typical experiment, 3 g of catalyst were placed in the reactor between two quartz wool plugs. All the parts were shielded from light. The catalyst was heated in air from room temperature to 500 C at a rate of 3 C/min and kept for 1 h at 500 C. Then, the catalyst was cooled down to the reaction temperature under nitrogen flow. Methane flow, controlled by a calibrated mass flow controller (Aalborg), entrained bromine vapor from a bromine reserve maintained at 2 C to give a methane to bromine ratio of 10.3 to 1. For bromination reactions, after 1 h on-stream, the products from the exit of the reactor were collected for 2 h in a solution of CDCl 3 kept at -60 C and analyzed by NMR (AS400 MHz Oxford) using dichloromethane as internal standard. The connection from the exit of the reactor to the sample collector was heated at 150 C to avoid condensation of the products. The flow from the CDCl 3 trap was passed through a 5 M NaOH aqueous solution. Samples could be taken at the entrance of the reactor, at the exit before and after the aqueous sodium hydroxide solution trap and analyzed off-line on two ThermoFiningan Trace GCs; one equipped with FID and TCD detectors using a 30 m Carboxen TM 1010 PLOT column from Supelco and the other with a FID detector using a 30 m GS-GASPRO column from Agilent. Chlorination samples were only analyzed by GC. When moisture was needed in the chlorination, methane was
3 passed into the water reservoir maintained at 22 C before combining with chlorine. For catalyst loadings of 5 g and above, the maximum pressure observed in the system did not exceed 30 psi. S3 Gas Chromatographic and NMR Spectral Analyses of Methane Chlorination and Bromination over H-SAPO-34 Chromatograms A 1 and B 1 were obtained on a ThermoFiningan Trace GC with TCD and FID detectors using a 30 m x 0.53 mm ID Carboxen TM 1010 PLOT column with the following oven temperature program: 35 C, 11.5 minutes, 10 C/min, 240 C, 5 minutes and Argon as the carrier gas. The retentions times (in minutes) for H 2, O 2, N 2, CO, CH 4, CO 2, and CH 3 Cl were 5.08, 11.86, 12.14, 14.38, 19.30, and 26.97, respectively. The peaks of N 2 and CH 4 are shown in the chromatograms. N 2 was used as the internal standard to calculate the conversion of CH 4. CO and CO 2 were not observed under the reaction conditions. CH 3 Cl and CH 2 Cl 2 did not show well on the FID chromatograms using the Carboxen TM 1010 PLOT column. Another ThermoFiningan Trace GC equipped with a 30 m x 0.53 mm ID GS-GASPRO column was used to obtain C 1 chromatograms to quantify CH 4 and the chloromethanes. The oven temperature program used was: 100 C, 2 minutes, 15 C/min, 240 C, 3 minutes with helium as the carrier gas. The peaks corresponding to the compounds are identified in the chromatograms. TCD and FID chromatograms obtained using the Carboxen TM 1010 PLOT column are shown for the thermal chlorination of CH 4 experiments at 350 C in the presence of moisture. When hydrocarbons were produced during the reaction, they were identified by comparing their peaks with those of pure authentic samples in the chromatograms. Samples for 1 H and 13 C NMR were collected for 2 h in CDCl 3 at 60 C and analyzed on an AS400 MHz Oxford NMR. CH 2 Cl 2 was used as an internal standard. The chemical shift of residual protons of CDCl 3 (7.26 ppm) was used as internal reference for 1 H NMR spectra and the carbon chemical shift (77.16 ppm) for 13 C NMR spectra. Various other species were also detected. List of Figures
4 1. Figure S1. Chlorination over 5 g of H-SAPO-34 at 350 ºC with time on-stream in the presence of moisture. CH 4 /Cl 2 /N 2 /H 2 O = 10:1:1.3:0.3. Total flow: 600 ml/h g. 2. Figure S2. Hydrocarbon phase composition in the chlorination of methane over H-SAPO- 34 at 350 ºC after 18 h and 22 h on-stream in the presence of moisture. 7 g of catalyst. CH 4 /Cl 2 /N 2 /H 2 O = 10:1:1.3:0.3. Total flow: 420 ml/min. 3. Figure S3. 1 H NMR of the product mixture in CDCl 3 (with CH 2 Cl 2 as internal standard) after bromination of CH 4 over H-SAPO-34 at 144 ml/g h, 365 o C, 3 h on-stream 4. Figure S4. 13 C NMR of the product mixture in CDCl 3 (with CH 2 Cl 2 as internal standard) after bromination of CH 4 over of H-SAPO-34 at 144 ml/g h, 365 o C, 3 h on-stream 5. Figure S5. Hydrocarbon phase composition in the bromination of methane over H-SAPO- 34 at 43.2 ml/g h (10 g of H-SAPO-34), 365 o C, 4 h on-stream. 6. Figure S6. FID Chromatogram of the bromination of CH 4 over of H-SAPO-34 at 43.2 ml/g h (10 g of H-SAPO-34), 365 o C, 4 h on-stream 7. Figures S7 to S18: (TCD) and (FID) chromatograms of the thermal chlorination of methane at 350 C in the presence of moisture with time on-stream using the Carboxen 1010 column and the GS-GASPRO column. 8. Figures S19 to S22: Chromatograms (FID - GS-GASPRO column) of the chlorination of methane over 3 g of H-SAPO-34 at 350 C with time on-stream and S23 and S24 after regeneration with oxygen. 9. Figures S25 to S31 (FID - GS-GASPRO column) chromatograms of the chlorination of methane over 5 g of H-SAPO-34 at 350 C with time on-stream in the presence of moisture. 10. Figures S32 to S36 (FID - GS-GASPRO column) chromatograms of the chlorination of methane over 7 g of H-SAPO-34 at 350 C with time on-stream in the presence of moisture. 11. Figures S37 and S38: 1 H (S37) and 13 C (S38) NMR spectra of the bromination of methane over 10 g of H-SAPO-34 at 345 C, 3 h on-stream. 12. Figures S39 and S40: 1 H (S39) and 13 C (S40) NMR spectra of the thermal bromination of methane (blank) at 365 C, 3 h on-stream. 13. Figures S41 and S42: 1 H (S41) and 13 C (S42) NMR spectra of the bromination of methane over 1 g of H-SAPO-34 mixed with 1 g of silica gel at 365 C, 3 h on-stream. 14. Figures S43 to S45: 1 H (S43 and S44) and 13 C (S45) NMR spectra of the bromination of methane over 10 g of H-SAPO-34 at 365 C, 4 h on-stream. 15. Figures S46 and S47: 1 H (S46) and 13 C (S47) NMR spectra of the bromination of methane over 10 g of H-SAPO-34 at 345 C, 10 h on-stream. 16. Figures S48 and S49: 1 H (S48) and 13 C (S49) NMR spectra of the bromination of methane over 3 g of H-SAPO-34 at 365 C, 9 h on-stream. S4
5 17. Figures S50 and S51: 1 H (S50) and 13 C (S51) NMR spectra of the bromination of methane over 3 g of H-SAPO-34 at 365 C, 15 h on-stream. S5 Schemes Scheme S1. Three-step conversion of methane to hydrocarbons developed by Olah et al. 1 Scheme S2. Two-step conversion of methane to hydrocarbons 2,3 Scheme S3. Methane bromination over H-SAPO-34. Scheme S4. One-step conversion of methane to hydrocarbons over H-SAPO-34. Tables Table S1. Chlorination over 7 g of H-SAPO-34 at 350 ºC in the presence of moisture Time (h) Conversion Cl 2 (mol%) Product distribution (mol%) Carbon balance (%)
6 S6 CH 3 Cl CH 2 Cl CH 4 /Cl 2 /N 2 /H 2 O = 10:1:1.3:0.3. Total flow: 420 ml/h g. 1 The rest is made of higher hydrocarbons; see Figure 2. Table S2. Bromination of methane over H-SAPO-34 Catalyst weight (g) T ( C) Conv. Br 2 (mol %) Product distribution (mol %) Carbon balance (%) CH 3 Br CH 2 Br 2 CHBr CH 4 /Br 2 molar ratio 10.3:1. Methane flow rate 7.2 ml/min. 3 h on-stream. 1 1 g of H-SAPO-34 mixed with 1 g of silica gel. 2 The rest is made of higher hydrocarbons; see Figures 5 and 6. Figures
7 S7 Figure S1. Chlorination over 5 g of H-SAPO-34 at 350 ºC with time on-stream in the presence of moisture. CH 4 /Cl 2 /N 2 /H 2 O = 10:1:1.3:0.3. Total flow: 600 ml/h g. Figure S2. Hydrocarbon phase composition in the chlorination of methane over H-SAPO-34 at 350 ºC after 18 h and 22 h on-stream in the presence of moisture. 7 g of catalyst. CH 4 /Cl 2 /N 2 /H 2 O = 10:1:1.3:0.3. Total flow: 420 ml/min.
8 S8 CH 2Cl 2 CH 3Br CDCl 3 ppm Figure S3. 1 H NMR of the product mixture in CDCl 3 (with CH 2 Cl 2 as internal standard) after bromination of CH 4 over H-SAPO-34 at 144 ml/g h, 365 o C, 3 h on-stream CDCl 3 CH 2Cl 2 CH 3Br ppm Figure S4. 13 C NMR of the product mixture in CDCl 3 (with CH 2 Cl 2 as internal standard) after bromination of CH 4 over of H-SAPO-34 at 144 ml/g h, 365 o C, 3 h on-stream
9 S9 Figure S5. Hydrocarbon phase composition in the bromination of methane over H-SAPO-34 at 43.2 ml/g h (10 g of H-SAPO-34), 365 o C, 4 h on-stream. Figure S6. FID Chromatogram of the bromination of CH 4 over of H-SAPO-34 at 43.2 ml/g h (10 g of H-SAPO-34), 365 o C, 4 h on-stream
10 S10 Additional Figures: GC and NMR spectra Figure S7. TCD spectrum of the product mixture from thermal chlorination of CH 4 at 350 o C in the presence of moisture, tos 0.5 h Figure S8. FID spectrum of the product mixture from thermal chlorination of CH 4 at 350 o C in the presence of moisture, tos 0.5 h
11 S11 Figure S9. FID spectrum of the product mixture from thermal chlorination of CH 4 at 350 o C in the presence of moisture, tos 0.5 h Figure S10. TCD (Carboxen column) spectrum of the product mixture from thermal chlorination of CH 4 at 350 o C in the presence of moisture, tos 2 h
12 S12 Figure S11. FID (Carboxen column) spectrum of the product mixture from thermal chlorination of CH 4 at 350 o C in the presence of moisture, tos 2 h Figure S12. TCD (GS-GasPro column) spectrum of the product mixture from thermal chlorination of CH 4 at C in the presence of moisture, tos 2 h
13 S13 Figure S13. TCD (Carboxen column) spectrum of the product mixture from thermal chlorination of CH 4 at 350 o C in the presence of moisture, tos 4 h Figure S14. FID (Carboxen column) spectrum of the product mixture from thermal chlorination of CH 4 at C in the presence of moisture, tos 4 h
14 S14 Figure S15. FID (GS-GasPro column) spectrum of product mixture from thermal chlorination of CH 4 at 350 o C in the presence of moisture, tos 4 h Figure S16. TCD (Carboxen column) spectrum of the product mixture from thermal chlorination of CH 4 at 350 o C in the presence of moisture, tos 24 h
15 S15 Figure S17. FID (Carboxen column) spectrum of the product mixture from thermal chlorination of CH 4 at 350 o C in the presence of moisture, tos 24 h Figure S18. FID (GS-GasPro column) spectrum of the product mixture from thermal chlorination of CH 4 at 350 o C in the presence of moisture, tos 24 h
16 S16 Figure S19. FID (GS-GasPro column) spectrum of the product mixture from chlorination of CH 4 at 350 o C over H-SAPO-34, tos 1 h Figure S20. FID (GS-GasPro column) spectrum of the product mixture from chlorination of CH 4 at 350 o C over H-SAPO-34, tos 2 h
17 S17 Figure S21. FID (GS-GasPro column) spectrum of the product mixture from chlorination of CH 4 at 350 o C over H-SAPO-34, tos 6 h Figure S22. FID (GS-GasPro column) spectrum of the product mixture from chlorination of CH 4 at 350 o C over H-SAPO-34, tos 22 h
18 S18 Reactions after regeneration of the catalyst with O 2 at 550 o C Figure S23. FID (GS-GasPro column) spectrum of the product mixture from chlorination of CH 4 at 350 o C over H-SAPO-34, tos 0.5 h Figure S24. FID (GS-GasPro column) spectrum of the product mixture from chlorination of CH 4 at 350 o C over H-SAPO-34, tos 4 h
19 Figure S25. FID (GS-GasPro column) spectrum of the product mixture from chlorination of CH 4 over 5 g of H-SAPO-34 at 350 o C in the presence of moisture, tos 0.25 h S19
20 S20 Figure S26. FID (GS-GasPro column) spectrum of the product mixture from chlorination of CH 4 over 5 g of H-SAPO-34 at 350 o C in the presence of moisture, tos 1.25 h Figure S27. FID (GS-GasPro column) chlorination of CH 4 over 5 g of H-SAPO-34 at 350 o C in the presence of moisture, tos 4 h
21 S21 Figure S28. FID (GS-GasPro column) spectrum of the product mixture from chlorination of CH 4 over 5 g of H-SAPO-34 at 350 o C in the presence of moisture, tos 7 h Figure S29. FID (GS-GasPro column) spectrum of the product mixture from chlorination of CH 4 over 5 g of H-SAPO-34 at 350 o C in the presence of moisture, tos 20 h
22 S22 Figure S30. FID (GS-GasPro column) spectrum of the product mixture from chlorination of CH 4 over 5 g of H-SAPO-34 at 350 o C in the presence of moisture, tos 24 h Figure S31. FID (GS-GasPro column) spectrum of the product mixture from chlorination of CH 4 over 5 g of H-SAPO-34 at 350 o C in the presence of moisture, tos 27 h
23 S23 Figure S32. FID (GS-GasPro column) spectrum of the product mixture from Chlorination of CH 4 over 7 g of H-SAPO-34 at 365 o C in the presence of moisture, tos 0.5 h Figure S33. FID (GS-GasPro column) spectrum of the product mixture fromchlorination of CH 4 over 7 g of H-SAPO-34 at 365 o C in the presence of moisture, tos 1 h
24 S24 Figure S34. FID (GS-GasPro column) spectrum of the product mixture from chlorination of CH 4 over 7 g of H-SAPO-34 at 365 o C in the presence of moisture, tos 2 h Figure S35. FID (GS-GasPro column) spectrum of the product mixture from chlorination of CH 4 over 7 g of H-SAPO-34 at 365 o C in the presence of moisture, tos 18 h
25 S25 Figure S36. FID (GS-GasPro column) spectrum of the product mixture from chlorination of CH 4 over 7 g of H-SAPO-34 at 365 o C in the presence of moisture, tos 22 h Figure S37. 1 H NMR spectrum of the product mixture from bromination of CH 4 over 10 g H- SAPO-34 at 345 o C, tos 3 h
26 S26 Figure S C NMR spectrum of the product mixture from bromination of CH 4 over 10 g H- SAPO-34 at 345 o C, tos 3 h Figure S39. 1 H NMR spectrum of the product mixture from Thermal bromination of CH 4 at 365 o C, tos 3 h
27 S27 Figure S C NMR spectrum of the product mixture from thermal bromination of CH 4 at 365 o C, tos 3 h Figure S41. 1 H NMR spectrum of the product mixture from bromination of CH 4 over 1 g of H- SAPO-34 mixed with 1 g of SiO 2 gel at 365 o C, tos 3 h
28 S28 Figure S C NMR spectrum of the product mixture from bromination of CH 4 over 1 g of H- SAPO-34 mixed with 1 g of SiO 2 gel at 365 o C, tos 3 h Figure S43. 1 H NMR spectrum of the product mixture from Bromination of CH 4 over 10 g of H- SAPO-34 at 365 o C, tos 4 h
29 S29 Figure S44. 1 H NMR signals of the product mixture in the region between ppm from bromination of CH 4 over 10 g of H-SAPO-34 at 365 o C, tos 4 h Figure S C NMR spectrum of the product mixture from bromination of CH 4 over 10 g of H- SAPO-34 at 365 o C, tos 4 h
30 S30 Figure S46. 1 H NMR spectrum Bromination of CH 4 over 10 g of H-SAPO-34 at 345 o C, tos 10 h Figure S C NMR spectrum of the product mixture from bromination of CH 4 over 10 g of H- SAPO-34 at 345 o C, tos 10 h
31 S31 Figure S48. 1 H NMR spectrum of the product mixture from bromination of CH 4 over 3 g of H- SAPO-34 at 365 o C, tos 9 h Figure S C NMR spectrum of the product mixture from bromination of CH 4 over 3 g of H- SAPO-34 at 365 o C, tos 9 h
32 S32 Figure S50. 1 H NMR spectrum of the product mixture from bromination of CH 4 over 3 g of H- SAPO-34 at 365 o C, tos 15 h Figure S C NMR spectrum of the product mixture obtained from bromination of CH 4 over 3 g of H-SAPO-34 at 365 o C, tos 15 h
33 S33 References (1) (a) Olah G. A. Acc. Chem. Res. 1987, 20, (b) Olah, G. A.; Gupta, B.; Farima, M.; Felberg, J. D.; Wai, M. I.; Husain, A. Karpeles, R.; Lammerstsma, K.; Melhotra, A. K.; Trivedi, N. J. J. Am. Chem. Soc. 1985, 107, (2) (a) Noceti, R. P.; Taylor, C. E. US Patent (b) Taylor, C. E.; Noceti, R. P.; Schehl, R. R. Stud. Surf. Sci. Catal. 1988, 36, (c) Schweizer, A. E.; Jones, M. E.; Hickman, D. A. US Patent (d) He, J.; Xu, T.; Wang, Z.; Zhang, Q.; Deng, W.; Wang, Y. Angew. Chem. Int. Ed. 2012, 51, (3) (a) Jens, K. J.; Halvorsen, S.; Ofstad, E. B. Stud. Surf. Sci. Catal. 1988, 36, (b) Nubel, P. O.; Satek, L. G.; Spangler, M. J.; Lutman, C. A.; Michaels, G. O. US Patent (4) Wilson, S.; Barger, P. Microporous Mesoporous Mat. 1999, 29,
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