Phosphorus-containing solid catalysts and reactions catalyzed thereby, including synthesis of p-xylene

Cho, Hong Je; Fan, Wei; Tsapatsis, Michael; Dauenhauer, Paul J.; Ren, Limin; Lobo, Raul

Phosphorus-containing solid catalysts and reactions catalyzed thereby, including synthesis of p-xylene

Patent · Tue Nov 15 04:00:00 EST 2022

OSTI ID:1986817

Cho, Hong Je; Fan, Wei; Tsapatsis, Michael; Dauenhauer, Paul J.; Ren, Limin; Lobo, Raul

Methods and phosphorus-containing solid catalysts for catalyzing dehydration of cyclic ethers (e.g., furans, such as 2,5-dimethylfuran) and alcohols (e.g., ethanol and isopropanol). The alcohols and cyclic ethers may be derived from biomass. One example includes a tandem Diels-Alder cycloaddition and dehydration of biomass-derived 2,5-dimethyl-furan and ethylene to renewable p-xylene. The phosphorus-containing solid catalysts are also active and selective for dehydration of alcohols to alkenes.

View Patent

Research Organization:: University of Minnesota, Minneapolis, MN (United States); University of Masachusetts, Amherst, MA (United States); University of Delaware, Newark, DE (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: SC0001004

Assignee:: Regents of the University of Minnesota (Minneapolis, MN); University of Massachusetts Amherst (Amherst, MA); University of Delaware (Newark, DE)

Patent Number(s):: 11,498,062

Application Number:: 16/337,603

OSTI ID:: 1986817

Country of Publication:: United States

Language:: English

References (52)

Detailed investigation of the lattice structure of zeolite ZSM-11 by a combination of solid-state NMR and synchrotron x-ray diffraction techniques Fyfe, Colin A.; Gies, Hermann; Kokotailo, George T. Journal of the American Chemical Society, Vol. 111, Issue 7, p. 2470-2474 https://doi.org/10.1021/ja00189a016	journal	March 1989
Layer Structure Preservation during Swelling, Pillaring, and Exfoliation of a Zeolite Precursor Maheshwari, Sudeep; Jordan, Edgar; Kumar, Sandeep Journal of the American Chemical Society, Vol. 130, Issue 4, p. 1507-1516 https://doi.org/10.1021/ja077711i	journal	January 2008
Direct dehydration of 1,3-butanediol into butadiene over aluminosilicate catalysts Jing, F.; Katryniok, B.; Araque, M. Catalysis Science & Technology, Vol. 6, Issue 15 https://doi.org/10.1039/C5CY02211H	journal	January 2016
MCM-36: The first pillared molecular sieve with zeoliteproperties Roth, W. J.; Kresge, C. T.; Vartuli, J. C. Studies in Surface Science and Catalysis https://doi.org/10.1016/S0167-2991(06)81236-X	book	January 1995
Tuning of nanostructured SBA-15 silica using phosphoric acid Pitchumani, Raghuraman; Li, Wenjiang; Coppens, Marc-Olivier Catalysis Today, Vol. 105, Issue 3-4 https://doi.org/10.1016/j.cattod.2005.06.002	journal	August 2005
Catalytic Behavior of Brønsted Acid Sites in MWW and MFI Zeolites with Dual Meso- and Microporosity Liu, Dongxia; Bhan, Aditya; Tsapatsis, Michael ACS Catalysis, Vol. 1, Issue 1 https://doi.org/10.1021/cs100042r	journal	December 2010
2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry Pace, Vittorio; Hoyos, Pilar; Castoldi, Laura ChemSusChem, Vol. 5, Issue 8 https://doi.org/10.1002/cssc.201100780	journal	August 2012
Zeolite-β grown epitaxially on SSZ-31 nanofibers Nair, Sankar; Tsapatsis, Michael; Villaescusa, Luis A. Chemical Communications, Issue 10 https://doi.org/10.1039/a900538b	journal	January 1999
From biomass to furan through decarbonylation of furfural under mild conditions Lejemble, Philippe; Gaset, Antoine; Kalck, Philippe Biomass, Vol. 4, Issue 4 https://doi.org/10.1016/0144-4565(84)90039-8	journal	January 1984
Synthesis of Self-Pillared Zeolite Nanosheets by Repetitive Branching Zhang, Xueyi; Liu, Dongxia; Xu, Dandan Science, Vol. 336, Issue 6089 https://doi.org/10.1126/science.1221111	journal	June 2012
A New, Yet Familiar, Lamellar Zeolite Tsapatsis, Michael; Fan, Wei ChemCatChem, Vol. 2, Issue 3, p. 246-248 https://doi.org/10.1002/cctc.200900278	journal	March 2010
Oriented Molecular Sieve Membranes by Heteroepitaxial Growth Jeong, Hae-Kwon; Krohn, John; Sujaoti, Khristina Journal of the American Chemical Society, Vol. 124, Issue 44 https://doi.org/10.1021/ja020947w	journal	November 2002
Sub-40 nm Zeolite Suspensions via Disassembly of Three-Dimensionally Ordered Mesoporous-Imprinted Silicalite-1 Lee, Pyung-Soo; Zhang, Xueyi; Stoeger, Jared A. Journal of the American Chemical Society, Vol. 133, Issue 3, p. 493-502 https://doi.org/10.1021/ja107942n	journal	January 2011
Biodegradation-inspired bioproduction of methylacetoin and 2-methyl-2,3-butanediol Jiang, Xinglin; Zhang, Haibo; Yang, Jianming Scientific Reports, Vol. 3, Issue 1 https://doi.org/10.1038/srep02445	journal	August 2013
Rapid synthesis of Sn-Beta for the isomerization of cellulosic sugars Chang, Chun-Chih; Wang, Zhuopeng; Dornath, Paul RSC Advances, Vol. 2, Issue 28 https://doi.org/10.1039/c2ra21381h	journal	January 2012
The monoclinic framework structure of zeolite H-ZSM-5. Comparison with the orthorhombic framework of as-synthesized ZSM-5 van Koningsveld, H.; Jansen, J. C.; van Bekkum, H. Zeolites, Vol. 10, Issue 4, p. 235-242 https://doi.org/10.1016/0144-2449(94)90134-1	journal	April 1990
One-Dimensional (1D) Nanostructured Materials for Energy Applications Machín, Abniel; Fontánez, Kenneth; Arango, Juan C. Materials, Vol. 14, Issue 10 https://doi.org/10.3390/ma14102609	journal	May 2021
What do we know about the acidity of solid acids? Gorte, R. J. Catalysis Letters, Vol. 62, Issue 1, p. 1-13 https://doi.org/10.1023/A:1019010013989	journal	January 1999
Metabolic engineering of Escherichia coli for direct production of 1,4-butanediol Yim, Harry; Haselbeck, Robert; Niu, Wei Nature Chemical Biology, Vol. 7, Issue 7 https://doi.org/10.1038/nchembio.580	journal	May 2011
Pores by Pillaring: Not Always a Maze Tsapatsis, Michael; Maheshwari, Sudeep Angewandte Chemie International Edition, Vol. 47, Issue 23, p. 4262-4263 https://doi.org/10.1002/anie.200705755	journal	May 2008
Conversion of Xylose to Furfural Using Lewis and Brønsted Acid Catalysts in Aqueous Media Choudhary, Vinit; Sandler, Stanley I.; Vlachos, Dionisios G. ACS Catalysis, Vol. 2, Issue 9 https://doi.org/10.1021/cs300265d	journal	August 2012
Ultra-selective cycloaddition of dimethylfuran for renewable p-xylene with H-BEA Chang, Chun-Chih; Green, Sara K.; Williams, C. Luke Green Chem., Vol. 16, Issue 2 https://doi.org/10.1039/C3GC40740C	journal	January 2014
Structure of the Silica Phase Extracted from Silica/(TPA)OH Solutions Containing Nanoparticles Kragten, David D.; Fedeyko, Joseph M.; Sawant, Kaveri R. The Journal of Physical Chemistry B, Vol. 107, Issue 37, p. 10006-10016 https://doi.org/10.1021/jp035110h	journal	September 2003
Spontaneous nucleation and growth of pure silica zeolite-? free of connectivity defects Camblor, Miguel A.; Corma, Avelino; Valencia, Susana Chemical Communications, Issue 20 https://doi.org/10.1039/cc9960002365	journal	January 1996
Pure-Silica-Zeolite MEL Low- k Films from Nanoparticle Suspensions Li, Zijian; Lew, Christopher M.; Li, Shuang The Journal of Physical Chemistry B, Vol. 109, Issue 18 https://doi.org/10.1021/jp0441893	journal	May 2005
Desilication: on the controlled generation of mesoporosity in MFI zeolites Groen, Johan C.; Moulijn, Jacob A.; Pérez-Ramírez, Javier J. Mater. Chem., Vol. 16, Issue 22 https://doi.org/10.1039/B517510K	journal	January 2006
Selective Hydrogenolysis of Polyols and Cyclic Ethers over Bifunctional Surface Sites on Rhodium–Rhenium Catalysts Chia, Mei; Pagán-Torres, Yomaira J.; Hibbitts, David Journal of the American Chemical Society, Vol. 133, Issue 32 https://doi.org/10.1021/ja2038358	journal	August 2011
Renewable p -Xylene from 2,5-Dimethylfuran and Ethylene Using Phosphorus-Containing Zeolite Catalysts Cho, Hong Je; Ren, Limin; Vattipalli, Vivek ChemCatChem, Vol. 9, Issue 3 https://doi.org/10.1002/cctc.201601294	journal	January 2017
Computed X-ray Powder Diffraction Patterns for Ultrasmall Zeolite Crystals Schlenker, J. L.; Peterson, B. K. Journal of Applied Crystallography, Vol. 29, Issue 2, p. 178-185 https://doi.org/10.1107/S0021889895014191	journal	April 1996
Methods for Characterizing Zeolite Acidity Farneth, W. E.; Gorte, R. J. Chemical Reviews, Vol. 95, Issue 3 https://doi.org/10.1021/cr00035a007	journal	May 1995
Periodic Arrangement of Silica Nanospheres Assisted by Amino Acids Yokoi, Toshiyuki; Sakamoto, Yasuhiro; Terasaki, Osamu Journal of the American Chemical Society, Vol. 128, Issue 42 https://doi.org/10.1021/ja065071y	journal	October 2006
Dehydration of 1,4-butanediol into 3-buten-1-ol catalyzed by ceria Sato, Satoshi; Takahashi, Ryoji; Sodesawa, Toshiaki Catalysis Communications, Vol. 5, Issue 8 https://doi.org/10.1016/j.catcom.2004.05.006	journal	August 2004
Dehydration of tetrahydropyran over TiO2-Al2O3 Shuikin, N. I.; An, V. V. Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, Vol. 9, Issue 8 https://doi.org/10.1007/BF00907677	journal	August 1960
Pillared MFI Zeolite Nanosheets of a Single-Unit-Cell Thickness Na, Kyungsu; Choi, Minkee; Park, Woojin Journal of the American Chemical Society, Vol. 132, Issue 12, p. 4169-4177 https://doi.org/10.1021/ja908382n	journal	March 2010
Palladium catalyzed hydrogenation of furan: optimization of production conditions for tetrahydrofuran Godawa, C.; Rigal, L.; Gaset, A. Resources, Conservation and Recycling, Vol. 3, Issue 4 https://doi.org/10.1016/0921-3449(90)90018-Y	journal	June 1990
Lewis acid zeolites for tandem Diels–Alder cycloaddition and dehydration of biomass-derived dimethylfuran and ethylene to renewable p-xylene Chang, Chun-Chih; Je Cho, Hong; Yu, Jingye Green Chemistry, Vol. 18, Issue 5 https://doi.org/10.1039/C5GC02164B	journal	January 2016
Efficient production of 1,3-butadiene in the catalytic dehydration of 2,3-butanediol Duan, Hailing; Yamada, Yasuhiro; Sato, Satoshi Applied Catalysis A: General, Vol. 491 https://doi.org/10.1016/j.apcata.2014.12.006	journal	February 2015
Dehydration of diols catalyzed by CeO2 Sato, Satoshi; Takahashi, Ryoji; Sodesawa, Toshiaki Journal of Molecular Catalysis A: Chemical, Vol. 221, Issue 1-2 https://doi.org/10.1016/j.molcata.2004.07.004	journal	November 2004
Review of old chemistry and new catalytic advances in the on-purpose synthesis of butadiene Makshina, Ekaterina V.; Dusselier, Michiel; Janssens, Wout Chem. Soc. Rev., Vol. 43, Issue 22 https://doi.org/10.1039/C4CS00105B	journal	January 2014
Amphiphilic organosilane-directed synthesis of crystalline zeolite with tunable mesoporosity Choi, Minkee; Cho, Hae Sung; Srivastava, Rajendra Nature Materials, Vol. 5, Issue 9 https://doi.org/10.1038/nmat1705	journal	August 2006
Dehydration of butanediols over CeO2 catalysts with different particle sizes Igarashi, Ai; Ichikawa, Naoki; Sato, Satoshi Applied Catalysis A: General, Vol. 300, Issue 1 https://doi.org/10.1016/j.apcata.2005.10.054	journal	January 2006
Simple Synthesis Route to Monodispersed SBA-15 Silica Rods Sayari, Abdelhamid; Han, Bao-Hang; Yang, Yong Journal of the American Chemical Society, Vol. 126, Issue 44 https://doi.org/10.1021/ja0478734	journal	November 2004
Two paths for the dehydration of 1,4-butandiol to divinyl with a tricalcium phosphate catalyst Freidlin, L. Kh.; Sharf, V. Z. Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, Vol. 9, Issue 9 https://doi.org/10.1007/BF00909833	journal	September 1960
Phosphorous-Modified Beta Zeolite and Its Performance in Vacuum Gas Oil Hydrocracking Activity Manrique, Cecilia; Guzmán, Alexander; Solano, Roger Energy & Fuels, Vol. 33, Issue 4 https://doi.org/10.1021/acs.energyfuels.8b04485	journal	March 2019
Branched Diol Monomers from the Sequential Hydrogenation of Renewable Carboxylic Acids Spanjers, Charles S.; Schneiderman, Deborah K.; Wang, Jay Z. ChemCatChem, Vol. 8, Issue 19 https://doi.org/10.1002/cctc.201600710	journal	August 2016
Production of isoprene from formaldehyde and isobutylene through 3-methylbutanediol-1,3 Sharf, V. Z.; Freidlin, L. Kh.; Oparina, G. K. Bulletin of the Academy of Sciences, USSR Division of Chemical Science, Vol. 14, Issue 9 https://doi.org/10.1007/BF01083812	journal	September 1965
Combined desilication and phosphorus modification for high-silica ZSM-5 zeolite with related study of hydrocarbon cracking performance Ding, Jian; Wang, Meng; Peng, Luming Applied Catalysis A: General, Vol. 503 https://doi.org/10.1016/j.apcata.2015.07.011	journal	August 2015
Biomass-Derived Butadiene by Dehydra-Decyclization of Tetrahydrofuran Abdelrahman, Omar A.; Park, Dae Sung; Vinter, Katherine P. ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 5 https://doi.org/10.1021/acssuschemeng.7b00745	journal	March 2017
Catalytic Hydrogenation of Furan and Substituted Furans on Platinum Smith, Hilton A.; Fuzek, John F. Journal of the American Chemical Society, Vol. 71, Issue 2 https://doi.org/10.1021/ja01170a013	journal	February 1949
Stable single-unit-cell nanosheets of zeolite MFI as active and long-lived catalysts Choi, Minkee; Na, Kyungsu; Kim, Jeongnam Nature, Vol. 461, Issue 7261, p. 246-249 https://doi.org/10.1038/nature08288	journal	September 2009
One-Step Catalytic Transformation of Carbohydrates and Cellulosic Biomass to 2,5-Dimethyltetrahydrofuran for Liquid Fuels Yang, Weiran; Sen, Ayusman ChemSusChem, Vol. 3, Issue 5 https://doi.org/10.1002/cssc.200900285	journal	April 2010
Catalytic reaction of 1,3-butanediol over solid acids Ichikawa, Naoki; Sato, Satoshi; Takahashi, Ryoji Journal of Molecular Catalysis A: Chemical, Vol. 256, Issue 1-2 https://doi.org/10.1016/j.molcata.2006.04.057	journal	August 2006

Similar Records

Kinetic regimes in the tandem reactions of H-BEA catalyzed formation of p-xylene from dimethylfuran

Journal Article · Sat Oct 24 20:00:00 EDT 2015 · Catalysis Science and Technology · OSTI ID:1387605

Tandem Diels-Alder Reaction of Dimethylfuran and Ethylene and Dehydration to para -Xylene Catalyzed by Zeotypic Lewis Acids

Journal Article · Mon Feb 27 19:00:00 EST 2017 · ChemCatChem · OSTI ID:1469842

Lewis acid zeolites for tandem Diels–Alder cycloaddition and dehydration of biomass-derived dimethylfuran and ethylene to renewable p-xylene

Journal Article · Mon Oct 26 20:00:00 EDT 2015 · Green Chemistry · OSTI ID:1387601

Phosphorus-containing solid catalysts and reactions catalyzed thereby, including synthesis of p-xylene

Citation Formats

References (52)

Similar Records

Related Subjects