Patents by Inventor Steven M. Bischof
Steven M. Bischof has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 11498889Abstract: A process to produce 1-octene and 1-decene includes (a) separating a composition containing an oligomer product—which contains from 15 to 80 mol % C6 olefins, from 20 to 80 mol % C8 olefins, and from 5 to 20 mol % C10+ olefins—into a first oligomer composition containing C6 alkanes and at least 85 mol % C6 olefins (e.g., 1-hexene), a second oligomer composition containing at least 85 mol % C8 olefins (e.g., 1-octene), and a heavies stream containing C10+ olefins, then (b) contacting a metathesis catalyst system with the first oligomer composition to form a first composition comprising C10 linear internal olefins, (c) contacting the C10 linear internal olefins with an isomerization hydrofunctionalization catalyst system to form a second composition containing a functionalized alkane, (d) retro-hydrofunctionalizing the functionalized alkane to form a third composition containing 1-decene, and (e) purifying the third composition to isolate a fourth composition containing at least 90 mol % 1-decene.Type: GrantFiled: September 10, 2021Date of Patent: November 15, 2022Inventors: Steven M. Bischof, James Hillier
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Patent number: 11492305Abstract: The present disclosure relates to a catalyst system comprising i) (a) a bicyclic 2-[(phosphinyl)aminyl] cyclic imine chromium salt or (b) a chromium salt and a bicyclic 2-[(phosphinyl)aminyl] cyclic imine and ii) an organoaluminum compound. The present disclosure also relate to a process comprising: a) contacting i) ethylene; ii) a catalyst system comprising (a) a 2-[(phosphinyl)aminyl] cyclic imine chromium salt complex or (b) a chromium salt and a bicyclic 2-[(phosphinyl)aminyl] cyclic imine; ii) an organoaluminum compound, and iii) optionally an organic reaction medium; and b) forming an oligomer product in a reaction zone.Type: GrantFiled: November 8, 2021Date of Patent: November 8, 2022Assignee: Chevron Phillips Chemical Company, LPInventors: Steven M. Bischof, Orson L. Sydora, Daniel H. Ess, Uriah J. Kilgore, Doo-Hyun Kwon
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Patent number: 11358914Abstract: A process comprising A) continuously introducing into a reaction zone i) ethylene, ii) an iron salt, iii) a pyridine bisimine, iv) an organoaluminum compound, and v) an organic reaction medium, and B) forming an oligomer product in the reaction zone, the reaction zone having i) an iron of the iron salt concentration in a range of 5×10?4 mmol/kg to 5×10?3 mmol/kg, ii) an aluminum of the organoaluminum compound to iron of the iron salt molar ratio in a range of 300:1 to 800:1, ii) an ethylene partial pressure in a range of 750 psig to 1200 psig, iv) an ethylene to organic reaction medium mass ratio in a range of 0.8 to 4.5, v) a temperature in a range of 75° C. to 95° C., and optionally vi) a hydrogen partial pressure of at least 5 psi.Type: GrantFiled: March 26, 2021Date of Patent: June 14, 2022Assignee: Chevron Phillips Chemical Company, LPInventors: Steven M. Bischof, Brooke L. Small
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Patent number: 11267909Abstract: Disclosed herein are oligomerization processes in which ethylene and a catalyst system are first combined for a suitable residence time in an activation vessel, prior to introduction into a reaction zone to oligomerize ethylene to form a desired oligomer product, such as 1-hexene and/or 1-octene. Related oligomerization reaction systems that include the activation vessel also are disclosed. In these oligomerization processes and reaction systems, the catalyst system can be fully activated as it leaves the activation vessel and enters the reaction zone, thus providing greater catalyst utilization and less catalyst waste.Type: GrantFiled: July 15, 2020Date of Patent: March 8, 2022Assignee: Chevron Phillips Chemical Company LPInventors: Steven M. Bischof, James L. Hillier, Uriah J. Kilgore, Steve R. Hutchison, Bruce E. Kreischer, Orson L. Sydora
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Publication number: 20220025081Abstract: Disclosed herein are oligomerization processes in which ethylene and a catalyst system are first combined for a suitable residence time in an activation vessel, prior to introduction into a reaction zone to oligomerize ethylene to form a desired oligomer product, such as 1-hexene and/or 1-octene. Related oligomerization reaction systems that include the activation vessel also are disclosed. In these oligomerization processes and reaction systems, the catalyst system can be fully activated as it leaves the activation vessel and enters the reaction zone, thus providing greater catalyst utilization and less catalyst waste.Type: ApplicationFiled: September 7, 2021Publication date: January 27, 2022Inventors: Steven M. Bischof, James L. Hillier, Uriah J. Kilgore, Steve R. Hutchison, Bruce E. Kreischer, Orson L. Sydora
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Publication number: 20220017660Abstract: Disclosed herein are oligomerization processes in which ethylene and a catalyst system are first combined for a suitable residence time in an activation vessel, prior to introduction into a reaction zone to oligomerize ethylene to form a desired oligomer product, such as 1-hexene and/or 1-octene. Related oligomerization reaction systems that include the activation vessel also are disclosed. In these oligomerization processes and reaction systems, the catalyst system can be fully activated as it leaves the activation vessel and enters the reaction zone, thus providing greater catalyst utilization and less catalyst waste.Type: ApplicationFiled: July 15, 2020Publication date: January 20, 2022Inventors: Steven M. Bischof, James L. Hillier, Uriah J. Kilgore, Steve R. Hutchison, Bruce E. Kreischer, Orson L. Sydora
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Patent number: 11123723Abstract: Catalyst compositions for the conversion of aldehyde compounds and primary alcohol compounds to olefins are disclosed herein. Reactions include oxidative dehydroxymethylation processes and oxidative dehydroformylation methods, which are beneficially conducted in the presence of a sacrificial acceptor of H2 gas, such as N,N-dimethylacrylamide.Type: GrantFiled: February 25, 2019Date of Patent: September 21, 2021Assignee: The Regents of the University of CaliforniaInventors: Vy M. Dong, Faben A. Cruz, Xuesong Wu, Steven M. Bischof, Stephen Karl Murphy
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Patent number: 11117845Abstract: A catalyst system comprising i) a 2-[(phosphinyl)aminyl] cyclic imine transition metal compound complex and ii) an organoaluminum compound. A process comprising contacting i) ethylene, ii) a catalyst system comprising (a) a 2-[(phosphinyl)aminyl] cyclic imine transition metal compound complex, and (b) an organoaluminum compound, and iii) optionally hydrogen to form an oligomer product.Type: GrantFiled: December 11, 2018Date of Patent: September 14, 2021Assignee: Chevron Phillips Chemical Company, LPInventors: Uriah J. Kilgore, Steven M. Bischof, Orson L. Sydora
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Patent number: 11072569Abstract: The present invention discloses processes for producing normal alpha olefins, such as 1-hexene, 1-octene, 1-decene, and 1-dodecene in a multistep synthesis scheme from another normal alpha olefin. Also disclosed are reactions for converting aldehydes, primary alcohols, and terminal vicinal diols into normal alpha olefins.Type: GrantFiled: July 6, 2020Date of Patent: July 27, 2021Assignee: Chevron Phillips Chemical Company LPInventors: Steven M. Bischof, Vy M. Dong, Faben A. Cruz, Xuesong Wu, Stephen Karl Murphy
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Publication number: 20210214289Abstract: A process comprising A) continuously introducing into a reaction zone i) ethylene, ii) an iron salt, iii) a pyridine bisimine, iv) an organoaluminum compound, and v) an organic reaction medium, and B) forming an oligomer product in the reaction zone, the reaction zone having i) an iron of the iron salt concentration in a range of 5×10?4 mmol/kg to 5×10?3 mmol/kg, ii) an aluminum of the organoaluminum compound to iron of the iron salt molar ratio in a range of 300:1 to 800:1, ii) an ethylene partial pressure in a range of 750 psig to 1200 psig, iv) an ethylene to organic reaction medium mass ratio in a range of 0.8 to 4.5, v) a temperature in a range of 75° C. to 95° C., and optionally vi) a hydrogen partial pressure of at least 5 psi.Type: ApplicationFiled: March 26, 2021Publication date: July 15, 2021Inventors: Steven M. BISCHOF, Brooke L. SMALL
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Patent number: 10927052Abstract: A composition comprising olefin oligomers of one or more olefin monomers, the olefin monomers comprising a branched C10 olefin monomer comprising i) 3-propyl-1-heptene, ii) 4-ethyl-1-octene, iii) 5-methyl-1-nonene, or iv) any combination thereof. A composition comprising substantially hydrogenated olefin oligomers, wherein the olefin oligomers are oligomers of one or more olefin monomers, the olefin monomers comprising a branched C10 olefin monomer comprising i) 3-propyl-1-heptene, ii) 4-ethyl-1-octene, iii) 5-methyl-1-nonene, or iv) any combination thereof. A process comprising a) contacting 1) a catalyst system and 2) a monomer feedstock comprising a branched C10 olefin monomer comprising i) 3-propyl-1-heptene, ii) 4-ethyl-1-octene, iii) 5-methyl-1-nonene, or iv) any combination thereof in a reaction zone; and b) forming olefin oligomers.Type: GrantFiled: March 6, 2020Date of Patent: February 23, 2021Assignee: Chevron Phillips Chemical Company LPInventors: Robert C. Coffin, Steven M. Bischof, Lauren M. Kattchee, Kenneth M. Lassen, Jason L. Kreider
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Publication number: 20200331823Abstract: The present invention discloses processes for producing normal alpha olefins, such as 1-hexene, 1-octene, 1-decene, and 1-dodecene in a multistep synthesis scheme from another normal alpha olefin. Also disclosed are reactions for converting aldehydes, primary alcohols, and terminal vicinal diols into normal alpha olefins.Type: ApplicationFiled: July 6, 2020Publication date: October 22, 2020Inventors: Steven M. Bischof, Vy M. Dong, Faben A. Cruz, Xuesong Wu, Stephen Karl Murphy
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Patent number: 10807921Abstract: Disclosed herein is a catalyst system comprising (i) a heterocyclic 2-[(phosphinyl)aminyl]imine transition metal compound complex having Structure I wherein T is oxygen or sulfur, R1 and R2 are each independently a C1 to C20 organyl group consisting essentially of inert functional groups, R3 is hydrogen or a C1 to C20 organyl group, L is a C1 to C20 organylene group consisting essentially of inert functional groups, MXp represents a transition metal compound where M is a transition metal, X is a monoanion, and p is an integer from 1 to 6, Q is a neutral ligand, and q ranges from 0 to 6, and (ii) an organoaluminum compound. Also disclosed herein is a process comprising contacting (i) ethylene, (ii) a catalyst system comprising (a) a heterocyclic transition metal compound complex having Structure I as described herein and (b) an organoaluminum compound, and (iii) optionally hydrogen to form an oligomer product.Type: GrantFiled: December 1, 2017Date of Patent: October 20, 2020Assignee: Chevron Phillips Chemical Company LPInventors: Uriah J. Kilgore, Steven M. Bischof
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Patent number: 10774015Abstract: Disclosed herein are processes, systems, and reaction systems for the oligomerization of ethylene to form an ethylene oligomer product in a reaction zone using a catalyst system having i) a chromium component comprising a heteroatomic ligand chromium compound complex of the type disclosed herein, and ii) an aluminoxane. A C3+ olefin can be present in the reaction zone for a period of time, where the C3+ olefin is not an ethylene oligomer formed in-situ within the reaction zone.Type: GrantFiled: August 21, 2019Date of Patent: September 15, 2020Assignee: Chevron Phillips Chemical Company LPInventors: Jared T. Fern, Orson L. Sydora, Uriah J. Kilgore, Steven M. Bischof, Eric R. Fernandez
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Patent number: 10745340Abstract: The invention provides processes and materials for the efficient and cost-effective functionalization of alkanes, such as methane from natural gas, to provide esters, alcohols, and other compounds. The method can be used to produce liquid fuels such as methanol from a natural gas methane-containing feedstock. The soft oxidizing electrophile, a compound of a main group, post-transitional element such as Tl, Pb, Bi, and I, that reacts to activate the alkane C—H bond can be regenerated using inexpensive regenerants such as hydrogen peroxide, oxygen, halogens, nitric acid, etc. Main group compounds useful for carrying out this reaction includes haloacetate salts of metals having a pair of available oxidation states, such as Tl, Pb, Bi, and I.Type: GrantFiled: February 25, 2014Date of Patent: August 18, 2020Assignee: The Scripps Research InstituteInventors: Roy A Periana, Brian G Hashiguchi, Michael M Konnick, Steven M Bischof
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Patent number: 10723672Abstract: The present invention discloses processes for producing normal alpha olefins, such as 1-hexene, 1-octene, 1-decene, and 1-dodecene in a multistep synthesis scheme from another normal alpha olefin. Also disclosed are reactions for converting aldehydes, primary alcohols, and terminal vicinal diols into normal alpha olefins.Type: GrantFiled: February 25, 2019Date of Patent: July 28, 2020Assignee: Chervon Phillips Chemical Company LPInventors: Steven M. Bischof, Vy M. Dong, Stephen Karl Murphy
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Publication number: 20200207682Abstract: A composition comprising olefin oligomers of one or more olefin monomers, the olefin monomers comprising a branched C10 olefin monomer comprising i) 3-propyl-1-heptene, ii) 4-ethyl-1-octene, iii) 5-methyl-1-nonene, or iv) any combination thereof. A composition comprising substantially hydrogenated olefin oligomers, wherein the olefin oligomers are oligomers of one or more olefin monomers, the olefin monomers comprising a branched C10 olefin monomer comprising i) 3-propyl-1-heptene, ii) 4-ethyl-1-octene, iii) 5-methyl-1-nonene, or iv) any combination thereof. A process comprising a) contacting 1) a catalyst system and 2) a monomer feedstock comprising a branched C10 olefin monomer comprising i) 3-propyl-1-heptene, ii) 4-ethyl-1-octene, iii) 5-methyl-1-nonene, or iv) any combination thereof in a reaction zone; and b) forming olefin oligomers.Type: ApplicationFiled: March 6, 2020Publication date: July 2, 2020Inventors: Robert C. Coffin, Steven M. Bischof, Lauren M. Kattchee, Kenneth M. Lassen, Jason L. Kreider
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Patent number: 10689311Abstract: Disclosed are processes, systems, and reaction systems for the oligomerization of ethylene to form an ethylene oligomer product in a reaction zone using a catalyst system comprising (a) a chromium component comprising an N2-phosphinyl amidine chromium compound complex, an N2-phosphinyl formamidine chromium compound complex, an N2-phosphinyl guanidine chromium compound complex, or any combination thereof, and (b) an aluminoxane. A C3+ olefin can be present in the reaction zone for a period of time, where the C3+ olefin is not an ethylene oligomer formed in-situ within the reaction zone.Type: GrantFiled: May 9, 2019Date of Patent: June 23, 2020Assignee: Chevron Phillips Chemical Company, LPInventors: Jared T. Fern, Orson L. Sydora, Uriah J. Kilgore, Steven M. Bischof, Eric R. Fernandez
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Patent number: 10689312Abstract: Disclosed are processes, systems, and reaction systems for the oligomerization of ethylene to form an oligomer product in a reaction zone using a catalyst system having i) a chromium component comprising an N2-phosphinyl amidine chromium compound complex, an N2-phosphinyl formamidine chromium compound complex, an N2-phosphinyl guanidine chromium compound complex, or any combination thereof, and ii) an aluminoxane. Ethylene can be contacted with an organic reaction medium to form an ethylene feedstock mixture prior to contact with the catalyst system. The ethylene feedstock mixture can be contacted with the catalyst system inside or outside of the reaction zone.Type: GrantFiled: August 21, 2019Date of Patent: June 23, 2020Assignee: Chevron Phillip Chemical Company, LPInventors: Steven M. Bischof, Orson L. Sydora, Jared T. Fern, Uriah J. Kilgore, Steven Ross Hutchison, Ray Rios, Eric R. Fernandez
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Patent number: 10647626Abstract: A composition comprising olefin oligomers of one or more olefin monomers, the olefin monomers comprising a branched C10 olefin monomer comprising i) 3-propyl-1-heptene, ii) 4-ethyl-1-octene, iii) 5-methyl-1-nonene, or iv) any combination thereof. A composition comprising substantially hydrogenated olefin oligomers, wherein the olefin oligomers are oligomers of one or more olefin monomers, the olefin monomers comprising a branched C10 olefin monomer comprising i) 3-propyl-1-heptene, ii) 4-ethyl-1-octene, iii) 5-methyl-1-nonene, or iv) any combination thereof. A process comprising a) contacting 1) a catalyst system and 2) a monomer feedstock comprising a branched C10 olefin monomer comprising i) 3-propyl-1-heptene, ii) 4-ethyl-1-octene, iii) 5-methyl-1-nonene, or iv) any combination thereof in a reaction zone; and b) forming olefin oligomers.Type: GrantFiled: July 12, 2016Date of Patent: May 12, 2020Assignee: Chevron Phillips Chemical Company LPInventors: Robert C. Coffin, Steven M. Bischof, Lauren M. Kattchee, Kenneth M. Lassen, Jason L. Kreider