Dehydrogenation Patents (Class 585/252)
-
Patent number: 11530171Abstract: In accordance with the purpose(s) of the present disclosure, as embodied and broadly described herein, the disclosure relates to a method for producing C4 olefins from acetylene using supported metal-based catalysts and metal-based promoters. The method is inexpensive, efficient, and environmentally sound. Additionally, the method is selective for C4 olefins and other value-added products based on changes to reaction parameters including temperature, feed gas composition, and promoter identity. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.Type: GrantFiled: April 19, 2021Date of Patent: December 20, 2022Assignee: West Virginia UniversityInventors: Jianli Hu, Qingyuan Li
-
Patent number: 11339105Abstract: According to one or more embodiments disclosed herein, methods for operating dehydrogenation processes during non-normal operating conditions, such as at start-up, shut-down, system recycle, or unit trip, are described. The methods may include contacting a feed stream with a catalyst in a reactor portion of a reactor system to form a reactor effluent stream, separating at least a portion of the reactor effluent stream from the catalyst, passing the catalyst to a catalyst processing portion and processing the catalyst, wherein processing the catalyst comprises contacting the catalyst with oxygen, passing the catalyst from the processing portion to the reactor portion, wherein the catalyst exiting the processing portion comprises at least 0.001 wt. % oxygen, and contacting the catalyst with supplemental hydrogen, the contacting removing at least a portion of the oxygen from the catalyst by a combustion reaction.Type: GrantFiled: August 15, 2019Date of Patent: May 24, 2022Assignee: Dow Global Technologies LLCInventors: Lin Luo, Matthew T. Pretz
-
Patent number: 11292755Abstract: Olefins may be produced from C4-C6 saturated hydrocarbons by systems and methods comprising passing a feed comprising C4-C6 saturated hydrocarbons and hydrogen into a dehydrogenation unit to produce a dehydrogenation effluent, passing at least a portion of the dehydrogenation effluent into a hydrogenation unit to produce a hydrogenation effluent, and passing at least a portion of the hydrogenation effluent into a cracking unit to produce a cracking effluent comprising olefins. The dehydrogenation unit includes a dehydrogenation catalyst, the hydrogenation unit includes a hydrogenation catalyst, and the cracking unit includes a cracking catalyst.Type: GrantFiled: June 15, 2020Date of Patent: April 5, 2022Assignee: Saudi Arabian Oil CompanyInventors: Mohammed Abdulmajeed Al-Daous, Hussam A. Bahlouli
-
Patent number: 11078134Abstract: The invention relates to a process for the production of an alkene by alkane oxidative dehydrogenation, comprising: (a) subjecting a stream comprising an alkane to oxidative dehydrogenation conditions, comprising contacting the alkane with oxygen in the presence of a catalyst comprising a mixed metal oxide, resulting in a stream comprising alkene, unconverted alkane, water, carbon dioxide, unconverted oxygen, carbon monoxide and optionally an alkyne; (b) removing water from at least part of the stream comprising alkene, unconverted alkane, water, carbon dioxide, unconverted oxygen, carbon monoxide and optionally an alkyne resulting from step (a), resulting in a stream comprising alkene, unconverted alkane, carbon dioxide, unconverted oxygen, carbon monoxide and optionally alkyne; (c) removing unconverted oxygen, carbon monoxide and optionally alkyne from at least part of the stream comprising alkene, unconverted alkane, carbon dioxide, unconverted oxygen, carbon monoxide and optionally alkyne resulting from sType: GrantFiled: February 20, 2018Date of Patent: August 3, 2021Assignee: Shell Oil CompanyInventors: Georgios Mitkidis, Guus Van Rossum, Maria San Roman Macia, Ronald Jan Schoonebeek, Michael Johannes Franciscus Maria Verhaak
-
Patent number: 11040928Abstract: A process and apparatus for converting an alkane to an olefin. In one embodiment, the process involves oxidative coupling of an alkane, e.g., methane, with an oxidant, such as air, to produce an olefin having twice the number of carbon atoms as the alkane, e.g., ethylene. In another embodiment, the process involves oxidative dehydrogenation of an alkane, e.g., ethane, with an oxidant to form an olefin having the same number of carbon atoms as the alkane, e.g., ethylene. The process involves passing a flow of the oxidant from a first flow passage through a porous medium; diffusing a flow of the alkane from a second flow passage into the porous medium; and contacting the reactant alkane and the oxidant in the presence of a catalyst within the porous medium to produce the olefin.Type: GrantFiled: February 12, 2019Date of Patent: June 22, 2021Assignee: PRECISION COMBUSTION, INC.Inventor: Jeffrey Weissman
-
Patent number: 10821432Abstract: Disclosed is an olefin production method including: pretreating a catalyst by providing reduction gas to an alumina type catalyst to produce olefin from the hydrocarbon including not less than 90 wt % of LPG (Stage 1); producing the olefin by providing the catalyst pretreated at Stage 1 into Riser of Fast Fluidization Regime to dehydrogenate the hydrocarbon (Stage 2); separating the mixture of the produced propylene and the catalyst used at Stage 2, and regenerating the separated catalyst (Stage 3); and recycling the catalyst regenerated at Stage 3 to the process of Stage 1 (Stage 4).Type: GrantFiled: May 1, 2018Date of Patent: November 3, 2020Assignees: SK GAS CO., LTD., KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGYInventors: Deuk Soo Park, Ung Gi Hong, Hyeongchan Ahn, Won Choon Choi, Yong Ki Park
-
Patent number: 10730811Abstract: A process for producing ethylene is proposed in which an ethane- and oxygen-containing reaction input is formed and a portion of the ethane and of the oxygen in the reaction input is converted into ethylene and into acetic acid by oxidative dehydrogenation to obtain a process gas, wherein the process gas contains the unconverted portion of the ethane and of the oxygen, the ethylene and the acetic acid and also water and wherein the process gas is subjected to a water quench. It is provided that the water quench comprises introducing the process gas into a scrubbing column (10, 20, 30, 40, 50) into which in at least two different column portions respective aqueous, liquid scrubbing medium streams are introduced and run in countercurrent to the process gas. A corresponding plant (100) likewise forms part of the subject matter of the invention.Type: GrantFiled: December 22, 2017Date of Patent: August 4, 2020Assignee: LINDE AKTIENGESELLSCHAFTInventors: Mathieu Zellhuber, Andreas Peschel, Helmut Fritz
-
Patent number: 10710945Abstract: Aromatic compositions useful in various applications, such as aromatic fluid solvents and high temperature heat transfer fluids, are provided herein. Also provided are advantageous methods for obtaining the aromatic compositions, utilizing hydroalkylation of precursor aromatic hydrocarbons such as benzene, toluene, xylene, and the like. Particularly preferred aromatic compositions include one or more of cycloalkylaromatic, dicycloalkylaromatic, biphenyl, terphenyl, and diphenyl oxide compounds. The aromatic compositions may be blended with an aromatic solvent or other aromatic fluid comprising one or more of alkylnaphthalenes, alkylbenzenes, and naphthalene, e.g., to form a useful aromatic fluid solvent, or the aromatic compositions may be utilized as high temperature heat transfer fluids (with or without additional blend components).Type: GrantFiled: August 3, 2016Date of Patent: July 14, 2020Assignee: ExxonMobil Chemical Patents Inc.Inventors: Teng Xu, Stephen M. Davis
-
Patent number: 10472304Abstract: The present invention relates to a hydrocarbon conversion catalyst comprising i) a catalyst, in oxidic form, metals M1, M2, M3 and M4, wherein: M1 is selected from Si, Al, Zr, and mixtures thereof; M2 is selected from Pt, Cr, and mixtures thereof; M3 is selected from W, Mo, Re and mixtures thereof; M4 is selected from Sn, K, Y, Yb and mixtures thereof; and ii) a hydrogen scavenger selected from at least one alkali and/or alkaline earth metal derivative, preferably in metallic, hydride, salt, complex or alloy form; as well as a hydrocarbon conversion process utilizing this catalyst.Type: GrantFiled: June 29, 2016Date of Patent: November 12, 2019Assignee: SMH Co., LtdInventors: Kongkiat Suriye, Amnart Jantharasuk, Wuttithep Jareewatchara
-
Patent number: 9896393Abstract: In a process for producing dialkylbiphenyl compounds, a feed comprising substituted cyclohexylbenzene isomers having the formula (I): wherein each of R1 and R2 is an alkyl group and wherein the feed comprises m % by weight of isomers in which R1 is in the 2-position, based on the total weight of substituted cyclohexylbenzene isomers in the feed; is transalkylated with a compound of formula (II): to produce a transalkylation product comprising substituted cyclohexylbenzene isomers having the formula (I) and including n % by weight of isomers in which R1 is in the 2-position, based on the total weight of substituted cyclohexylbenzene isomers in the transalkylation product, wherein n<m. At least part of the transalkylation product is then dehydrogenated under conditions effective to convert at least part of the substituted cyclohexylbenzene isomers in the transalkylation product to dialkylbiphenyl compounds.Type: GrantFiled: May 28, 2015Date of Patent: February 20, 2018Assignee: ExxonMobil Chemical Patents Inc.Inventors: Michael Salciccioli, Tan-Jen Chen, Neeraj Sangar, Ali A. Kheir, Aaron B. Pavlish
-
Patent number: 9725377Abstract: This invention relates to process for producing biphenyl esters, the process comprising: (a) contacting a feed comprising toluene, xylene or mixtures thereof with hydrogen in the presence of a hydroalkylation catalyst to produce a hydroalkylation reaction product comprising (methylcyclohexyl)toluene, wherein the hydroalkylation catalyst comprises: 1) binder present at 40 wt % or less (based upon weight of final catalyst composition), 2) a hydrogenation component present at 0.2 wt % or less (based upon weight of final catalyst composition), and 3) an acidic component comprising a molecular sieve having a twelve membered (or larger) ring pore opening, channel or pocket and a largest pore dimension of 6.Type: GrantFiled: June 25, 2014Date of Patent: August 8, 2017Assignee: ExxonMobil Chemical Patents Inc.Inventors: Emiel de Smit, Neeraj Sangar, Michael Salciccioli, Jihad M. Dakka, Lorenzo C. DeCaul, Terry E. Helton, Scott J. Weigel
-
Patent number: 9708230Abstract: In a process for producing biphenyl compounds, a Cn aromatic hydrocarbon may be hydroalkylated to give C2n cycloalkylaromatic compounds and byproduct Cn saturated cyclic hydrocarbons. The C2n cycloalkylaromatic compounds are dehydrogenated to provide the biphenyl compounds. The Cn saturated cyclic hydrocarbons may also be dehydrogenated back to the corresponding Cn aromatic hydrocarbon, which may be recycled to provide additional feed. Although both the intermediate C2n cycloalkylaromatic compounds and the byproduct Cn saturated cyclic hydrocarbons should be dehydrogenated, at least part of the dehydrogenation of the Cn saturated cyclic hydrocarbons should take place in the absence of C2n or greater hydrocarbons. Thus, dehydrogenation of the byproduct Cn saturated cyclic hydrocarbons should take place at least in part separately from dehydrogenation of the C2n cycloalkylaromatic compounds.Type: GrantFiled: December 21, 2015Date of Patent: July 18, 2017Assignee: ExxonMobil Chemical Patents Inc.Inventors: Michael Salciccioli, Jihad M. Dakka, Neeraj Sangar, Lorenzo C. DeCaul, Ali A. Kheir
-
Patent number: 9688602Abstract: In a process for producing a methyl-substituted biphenyl compound, at least one methyl-substituted cyclohexylbenzene compound of the formula: wherein each of m and n is independently an integer from 1 to 3, is contacted with a dehydrogenation catalyst under conditions effective to produce a dehydrogenation reaction product comprising at least one methyl-substituted biphenyl compound. The dehydrogenation catalyst comprises an element or compound thereof from Group 10 of the Periodic Table of Elements deposited on a refractory support, such as alumina.Type: GrantFiled: March 7, 2014Date of Patent: June 27, 2017Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad M. Dakka, Chuansheng Bai, James J. Tanke, Gregory J. De Martin, Mary T. Van Nostrand, Michael Salciccioli, Ali A. Kheir, Neeraj Sangar
-
Patent number: 9663417Abstract: In a process for producing methyl-substituted biphenyl compounds, a feed comprising at least one aromatic hydrocarbon selected from the group consisting of toluene, xylene and mixtures thereof is contacted with hydrogen in the presence of a hydroalkylation catalyst under conditions effective to produce a hydroalkylation reaction product comprising (methylcyclohexyl)toluenes and/or (dimethylcyclohexyl)xylenes. At least part of the hydroalkylation reaction product is then dehydrogenated in the presence of a dehydrogenation catalyst under conditions effective to produce a dehydrogenation reaction product comprising a mixture of methyl-substituted biphenyl compounds.Type: GrantFiled: March 7, 2014Date of Patent: May 30, 2017Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad M. Dakka, Lorenzo C. DeCaul
-
Patent number: 9464166Abstract: In a process for producing 3,4? and/or 4,4? dimethyl-substituted biphenyl compounds, a feed comprising toluene is contacted with hydrogen in the presence of a hydroalkylation catalyst under conditions effective to produce a hydroalkylation reaction product comprising (methylcyclohexyl)toluenes. At least part of the hydroalkylation reaction product is dehydrogenated in the presence of a dehydrogenation catalyst under conditions effective to produce a dehydrogenation reaction product comprising a mixture of dimethyl-substituted biphenyl isomers. The dehydrogenation reaction product is then separated into at least a first stream containing at least 50% of 3,4? and 4,4? dimethylbiphenyl isomers by weight of the first stream and at least one second stream comprising one or more 2,x? (where x? is 2?, 3?, or 4?) and 3,3? dimethylbiphenyl isomers.Type: GrantFiled: September 8, 2014Date of Patent: October 11, 2016Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad M. Dakka, Lorenzo C. DeCaul, Keith H. Kuechler, Neeraj Sangar, Michael Salciccioli, Alan A. Galuska, Gary D. Mohr
-
Patent number: 9365467Abstract: In a process for producing cyclohexylbenzene, benzene is contacted with hydrogen under hydroalkylation conditions effective to form a first effluent stream comprising cyclohexylbenzene, cyclohexane, methylcyclopentane, and unreacted benzene. At least a portion of the first effluent stream is contacted with a dehydrogenation catalyst under dehydrogenation conditions to convert at least a portion of the cyclohexane to benzene thereby forming a second effluent stream. The amount of methylcyclopentane in the second effluent stream is different by no more than 65% of the total amount of the portion of the first effluent stream, said amounts being on a weight basis. A methylcyclopentane-containing stream is removed from either the first or the second effluent stream and at least a portion of the second effluent stream containing benzene is recycled to the hydroalkylation step.Type: GrantFiled: December 2, 2011Date of Patent: June 14, 2016Assignee: ExxonMobil Chemical Patents Inc.Inventors: Keith H. Kuechler, James R. Lattner, Christopher L. Becker, Jihad M. Dakka, Tan-Jen Chen
-
Patent number: 9328053Abstract: In a process for producing a methyl-substituted biphenyl compound, at least one methyl-substituted cyclohexylbenzene compound of the formula: is contacted with a dehydrogenation catalyst under conditions effective to produce a dehydrogenation reaction product comprising at least one methyl-substituted biphenyl compound, wherein each of m and n is independently an integer from 1 to 3 and wherein the dehydrogenation catalyst comprises (i) an element or compound thereof from Group 10 of the Periodic Table of Elements and (ii) tin or a compound thereof.Type: GrantFiled: March 7, 2014Date of Patent: May 3, 2016Assignee: ExxonMobil Chemical Patents Inc.Inventors: Chuansheng Bai, Jihad M. Dakka, Lorenzo C. DeCaul
-
Patent number: 9321704Abstract: A cyclohexane dehydrogenation process comprising a step of providing, as a benzene-containing stream, a vapor phase in equilibrium with a liquid phase at a condensation separation system; supplying benzene, hydrogen, and cyclohexane into a dehydrogenation reactor where at least part of the benzene supplied is from the benzene-containing stream. The use of a condensation separation system enables the control of the partial pressure of benzene in the material fed into the dehydrogenation reactor by controlling the temperature of the vapor phase, and hence the control of hydrogen to benzene molar ratio in the dehydrogenation reactor. The process results in a long life of the dehydrogenation catalyst due to reduced coking.Type: GrantFiled: December 2, 2013Date of Patent: April 26, 2016Assignee: ExxonMobil Chemical Patents Inc.Inventors: James R. Lattner, Christopher L. Becker, Tan-Jen Chen
-
Publication number: 20150126782Abstract: In a process for producing cyclohexylbenzene, hydrogen, and benzene are contacted in a first reaction zone under conditions effective to produce a product effluent containing residual benzene in the vapor phase and cyclohexylbenzene in the liquid phase. The product effluent is separated into a first stream that is rich in residual benzene in the vapor phase as compared to the product effluent and a second stream that is rich in cyclohexylbenzene in the liquid phase as compared to the product effluent. At least a portion of the first stream is cooled to condense at least a portion of the residual benzene in the vapor phase to the liquid phase and produce a condensate stream. At least a portion of the condensate stream is recycled to the first reaction zone.Type: ApplicationFiled: September 5, 2012Publication date: May 7, 2015Applicant: ExxonMobil Chemical Company - Law TechnologyInventors: Hari Nair, Christopher L. Becker, James R. Lattner, Jihad M. Dakka
-
Patent number: 8969639Abstract: In a dehydrogenation process a hydrocarbon stream comprising at least one non-aromatic six-membered ring compound and at least one five-membered ring compound is contacted with a dehydrogenation catalyst produced by a method comprising treating the support with a liquid composition comprising the dehydrogenation component or a precursor thereof and at least one organic dispersant selected from an amino alcohol and an amino acid. The contacting is conducted under conditions effective to convert at least a portion of the at least one non-aromatic six-membered ring compound in the hydrocarbon stream to benzene and to convert at least a portion of the at least one five-membered ring compound in the hydrocarbon stream to paraffins.Type: GrantFiled: December 17, 2010Date of Patent: March 3, 2015Assignee: ExxonMobil Chemical Patents Inc.Inventors: Teng Xu, Stuart L. Soled, Edward A. Lemon, Jr., Christine E. Kliewer, Tan-Jen Chen, Joseph E. Baumgartner, Sabato Miseo
-
Publication number: 20150057477Abstract: Methods and systems are provided for producing a fuel from a renewable feedstock. The method includes deoxygenating the renewable feedstock with a hydrogenation catalyst in a deoxygenation reaction zone to produce normal paraffins. The normal paraffins are isomerized to form isomerized paraffins using an isomerization catalyst in an isomerization reaction zone. Aromatic compounds are formed from non-aromatic compounds with an aromatic catalyst in an aromatic production zone downstream from the deoxygenation reaction zone.Type: ApplicationFiled: August 23, 2013Publication date: February 26, 2015Applicant: UOP LLCInventors: Daniel Ellig, Stanley Joseph Frey, Timothy A. Brandvold
-
Publication number: 20150045596Abstract: In a process for producing cyclohexylbenzene, benzene is contacted with hydrogen in the presence of a hydroalkylation catalyst under hydroalkylation conditions effective to form a first effluent stream comprising cyclohexylbenzene, cyclohexane, and benzene. At least a portion of the cyclohexane from the first effluent stream is then contacted with hydrogen in the presence of a dehydrogenation catalyst under dehydrogenation conditions effective to convert at least some of the cyclohexane into benzene contained in a second effluent stream. At least some of the hydrogen is supplied to the process so as to contact the dehydrogenation zone (e.g., the dehydrogenation catalyst) before contacting the hydroalkylation catalyst.Type: ApplicationFiled: December 5, 2012Publication date: February 12, 2015Inventors: Christopher L. Becker, James R. Lattner, Keith H. Kuechler, Hari Nair
-
Publication number: 20150011812Abstract: In a process for producing cyclohexylbenzene, hydrogen and benzene are introduced to a first hydroalkylation reaction zone which contains a hydroalkylation catalyst and which is operated under at least partly liquid phase conditions sufficient to effect hydroalkylation of benzene to produce a mixed liquid/vapor phase effluent comprising cyclohexylbenzene and unreacted benzene, wherein at least a portion of the unreacted benzene is in the vapor phase. At least a portion of the effluent is cooled to condense a liquid phase stream containing at least some of the cyclohexylbenzene in the effluent portion and leave a residual stream containing at least some of the unreacted benzene and cyclohexylbenzene. At least a portion of the liquid stream is recycled to the first hydroalkylation reaction zone or to contact the mixed phase effluent exiting the first hydroalkylation reaction zone. Other methods of cooling the reaction effluent are disclosed.Type: ApplicationFiled: January 28, 2013Publication date: January 8, 2015Inventors: Christopher L. Becker, Hari Nair, James R. Lattner, Keith H. Kuechler
-
Publication number: 20150005531Abstract: In a process for producing phenol, benzene is hydroalkylated with hydrogen in the presence of a catalyst under conditions effective to produce a hydroalkylation reaction product comprising cyclohexylbenzene and cyclohexane. At least a portion of the cyclohexane from said hydroalkylation reaction product is then dehydrogenated to produce a dehydrogenation effluent comprising benzene, toluene and hydrogen. At least a portion of the dehydrogenation effluent is washed with a benzene-containing stream to transfer at least a portion of the toluene from the dehydrogenation effluent to the benzene-containing stream.Type: ApplicationFiled: November 30, 2012Publication date: January 1, 2015Applicant: ExxonMobil Chemical Patents Inc.Inventors: Christopher L. Becker, James R. Lattner, Keith H. Kuechler, Hari Nair
-
Publication number: 20140378697Abstract: This invention relates to process for producing biphenyl esters, the process comprising: (a) contacting a feed comprising toluene, xylene or mixtures thereof with hydrogen in the presence of a hydroalkylation catalyst to produce a hydroalkylation reaction product comprising (methylcyclohexyl)toluene, wherein the hydroalkylation catalyst comprises: 1) binder present at 40 wt % or less (based upon weight of final catalyst composition), 2) a hydrogenation component present at 0.2 wt % or less (based upon weight of final catalyst composition), and 3) an acidic component comprising a molecular sieve having a twelve membered (or larger) ring pore opening, channel or pocket and a largest pore dimension of 6.Type: ApplicationFiled: June 25, 2014Publication date: December 25, 2014Inventors: Emiel de Smit, Neeraj Sangar, Michael Salciccioli, Jihad M. Dakka, Lorenzo C. DeCaul, Terry E. Helton, Scott J. Weigel
-
Publication number: 20140371498Abstract: In a process for producing cyclohexylbenzene, benzene is contacted with hydrogen under hydroalkylation conditions effective to form a first effluent stream comprising cyclohexylbenzene, cyclohexane, methylcyclopentane, and unreacted benzene. At least a portion of the first effluent stream is contacted with a dehydrogenation catalyst under dehydrogenation conditions to convert at least a portion of the cyclohexane to benzene thereby forming a second effluent stream. The amount of methylcyclopentane in the second effluent stream is different by no more than 65% of the total amount of the portion of the first effluent stream, said amounts being on a weight basis. A methylcyclopentane-containing stream is removed from either the first or the second effluent stream and at least a portion of the second effluent stream containing benzene is recycled to the hydroalkylation step.Type: ApplicationFiled: December 2, 2011Publication date: December 18, 2014Applicant: ExxonMobil Chemical Company - Law TechnologyInventors: Keith H. Kuechler, James R. Lattner, Christopher L. Becker, Jihad M. Dakka, Tan-Jen Chen
-
Publication number: 20140316155Abstract: In a process for producing methyl-substituted biphenyl compounds, a feed comprising at least one aromatic hydrocarbon selected from the group consisting of toluene, xylene and mixtures thereof is contacted with hydrogen in the presence of a hydroalkylation catalyst under conditions effective to produce a hydroalkylation reaction product comprising (methylcyclohexyl)toluenes and/or (dimethylcyclohexyl)xylenes together with dialkylated C21+ compounds. At least part of the dialkylated C21+ compounds is then removed from the hydroalkylation reaction product to produce a dehydrogenation feed; and at least part of the dehydrogenation feed is dehydrogenated in the presence of a dehydrogenation catalyst under conditions effective to produce a dehydrogenation reaction product comprising a mixture of methyl-substituted biphenyl compounds.Type: ApplicationFiled: March 7, 2014Publication date: October 23, 2014Inventors: Jihad M. Dakka, Lorenzo C. DeCaul, Victor DeFlorio
-
Publication number: 20140296587Abstract: A process is present for increasing the yields of 1,3 butadiene. The process includes recovering 1,3 butadiene from a cracking unit that generates a crude C4 stream. The 1,3 butadiene is separated and the remaining C4 process stream components are further reacted and dehydrogenated to generate 1,3 butadiene in a subsequent process stream. The subsequent process stream is recycled to recover the additional 1,3 butadiene.Type: ApplicationFiled: March 28, 2013Publication date: October 2, 2014Applicant: UOP LLCInventors: Andrea G. Bozzano, Bipin V. Vora, Daniel H. Wei, Steven L. Krupa
-
Publication number: 20140275605Abstract: A composition is described comprising a mixture of (methylcyclohexyl)toluene isomers having the following formula: wherein the mixture comprises at least 50 wt % in total of the 3,3, 3,4 4,3 and 4,4-isomers of (methylcyclohexyl)toluene.Type: ApplicationFiled: March 7, 2014Publication date: September 18, 2014Inventors: Jihad M. Dakka, Lorenzo C. DeCaul, Wei Tang
-
Publication number: 20140249339Abstract: Oxidative dehydrogenation of paraffins to olefins provides a lower energy route to produce olefins. Oxidative dehydrogenation processes may be integrated with a number of processes in a chemical plant such as polymerization processes, manufacture of glycols, and carboxylic acids and esters. Additionally, oxidative dehydrogenation processes can be integrated with the back end separation process of a conventional steam cracker to increase capacity at reduced cost.Type: ApplicationFiled: March 4, 2013Publication date: September 4, 2014Applicant: NOVA Chemicals (International) S.A.Inventors: Vasily Simanzhenkov, Leonid Modestovich Kustov, Aleksey Victorovich Kucherov, Elena Dmitrievna Finashina, Xiaoliang Gao, Edward Christopher Foy, Claire Jeannine Ennis
-
Patent number: 8758722Abstract: Provided is a method for producing hydrogen aimed at storage and transportation, by which hydrogen for storage and transportation that is necessary for smoothly performing an organic chemical hydride method can be industrially produced efficiently at low cost. The method is a method for producing hydrogen aimed at storage and transportation in an organic chemical hydride method, in which: the hydrogenation process of an aromatic compound uses, as a hydrogen source for the reaction of the aromatic compound, a reaction gas is produced by a reforming reaction and adjusted a hydrogen concentration from 30 to 70 vol % by a shift reaction; and a hydrogenated aromatic compound is separated from a reaction mixture obtained in the hydrogenation process, which is followed by purification.Type: GrantFiled: March 24, 2011Date of Patent: June 24, 2014Assignee: Chiyoda CorporationInventors: Yoshimi Okada, Masashi Saito, Shuhei Wakamatsu, Mitsunori Shimura
-
Publication number: 20140171702Abstract: Methods and apparatuses for increasing an alkyl-cyclopentane concentration in an aromatic-rich stream and methods for processing hydrocarbons are provided. In an embodiment, a method for increasing an alkyl-cyclopentane concentration in an aromatic-rich stream includes saturating aromatics in the aromatic-rich stream to form methylcyclohexane. Further, the method includes isomerizing the methylcyclohexane to form alkyl-cyclopentanes. The method dehydrogenates residual methylcyclohexane to form aromatics in a product stream. The product stream includes aromatics and alkyl-cyclopentanes.Type: ApplicationFiled: December 14, 2012Publication date: June 19, 2014Applicant: UOP LLCInventor: Bryan K. Glover
-
Publication number: 20140058146Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The method includes processing the acetylene to form a stream having butadiene. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream is be treated to convert acetylene to butadiene. The method according to certain aspects includes controlling the level of carbon monoxide to prevent undesired reactions in downstream processing units.Type: ApplicationFiled: June 11, 2013Publication date: February 27, 2014Inventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin, Debarshi Majumder
-
Publication number: 20130261342Abstract: A process for the telomerization of butadiene comprises reacting 1,3-butadiene and an alkanol, in the presence of a catalyst promoter and an alkoxydimerization catalyst comprising a Group VIII transition metal and a triarylphosphine ligand, which includes one phenyl that is mono-ortho-alkoxy substituted and at least one other phenyl including at least one substituent that withdraws electrons from the phosphorus atom. The product includes an alkoxy-substituted octadiene, which may then be used to produce 1-octene. The catalyst shows improved stability, activity and selectivity toward the alkoxy-substituted octadiene.Type: ApplicationFiled: December 14, 2011Publication date: October 3, 2013Applicant: Dow Global Technologies LLCInventors: John R. Briggs, Jasson T. Patton, Daryoosh Beigzadeh, Peter M. Margl, Henk Hagen, Sonet Vermaire-Louw
-
Patent number: 8450543Abstract: Isobutene, isoprene, and butadiene are obtained from mixtures of C4 and/or C5 olefins by dehydrogenation. The C4 and/or C5 olefins can be obtained by dehydration of C4 and C5 alcohols, for example, renewable C4 and C5 alcohols prepared from biomass by thermochemical or fermentation processes. Isoprene or butadiene can be polymerized to form polymers such as polyisoprene, polybutadiene, synthetic rubbers such as butyl rubber, etc. in addition, butadiene can be converted to monomers such as methyl methacrylate, adipic acid, adiponitrile, 1,4-butadiene, etc. which can then be polymerized to form nylons, polyesters, polymethylmethacrylate etc.Type: GrantFiled: January 7, 2011Date of Patent: May 28, 2013Assignee: Gevo, Inc.Inventors: Matthew W. Peters, Joshua D. Taylor, David E. Henton, Leo E. Manzer, Patrick R. Gruber, Josefa M. Griffith, Yassin Al Obaidi
-
Publication number: 20130060070Abstract: The invention relates to methods for producing fluid hydrocarbon products, and more specifically, to methods for producing fluid hydrocarbon product via catalytic pyrolysis. The reactants comprise solid hydrocarbonaceous materials, and hydrogen or a source of hydrogen (e.g., an alcohol). The products may include specific aromatic compounds (e.g., benzene, toluene, naphthalene, xylene, etc.).Type: ApplicationFiled: August 13, 2012Publication date: March 7, 2013Applicant: UNIVERSITY OF MASSACHUSETTSInventors: George W. Huber, Huiyan Zhang, Torren Carlson
-
Publication number: 20120283494Abstract: In a dehydrogenation process a hydrocarbon stream comprising at least one non-aromatic six-membered ring compound and at least one five-membered ring compound is contacted with a first catalyst comprising at least one metal component and at least one support and a second catalyst. The first catalyst is utilized to convert at least a portion of the at least one non-aromatic six-membered ring compound in the hydrocarbon stream to at least one aromatic compound and the second catalyst is utilized to convert at least a portion of the at least one five-membered ring compound in the hydrocarbon stream to at least one paraffin.Type: ApplicationFiled: December 17, 2010Publication date: November 8, 2012Inventors: Charles M. Smith, Tan-Jen Chen, Terry E. Helton, Teng Xu
-
Publication number: 20120271076Abstract: A process is described for producing a catalyst composition comprising an iridium component dispersed on a support. In the process, silica-containing support is treated with an iridium compound and an organic compound comprising an amino group to form an organic iridium complex on the support. The treated support is then heated in an oxidizing atmosphere at a temperature of about 325° C. to about 475° C. to partially decompose the organic metal complex on the support. The treated support is then heated in a reducing atmosphere at a temperature of about 350° C. to about 500° C. to convert the partially decomposed organic iridium complex into the desired iridium component.Type: ApplicationFiled: December 17, 2010Publication date: October 25, 2012Inventors: Stuart L. Soled, Sabato Miseo, Joseph E. Baumgartner, Christine E. Kliewer, Jane C. Cheng
-
Publication number: 20120271079Abstract: A processes for producing a dehydrogenation reaction product stream comprising the step of contacting a hydrocarbon stream comprising cyclohexane and methyl cyclopentane with a dehydrogenation catalyst comprising at least one metal or compound thereof and at least one molecular sieve and under conditions effective to convert at least a portion of the cyclohexane to benzene and to convert at least a portion of the methyl cyclopentane to at least one paraffin. The hydrocarbon stream is produced by hydroalkylating benzene and hydrogen to form a hydroalkylation reaction product stream which is separated to yield the hydrocarbon stream.Type: ApplicationFiled: December 17, 2010Publication date: October 25, 2012Inventors: Teng Xu, Edward A. Lemon, JR., Tan-Jen Chen, Terry E. Helton
-
Publication number: 20120271078Abstract: In a dehydrogenation process a hydrocarbon stream comprising at least one non-aromatic six-membered ring compound and at least one five-membered ring compound is contacted with a dehydrogenation catalyst comprising: (i) a support; (ii) a first component comprising at least one metal component selected from Group 1 and Group 2 of the Periodic Table of Elements; and (iii) a second component comprising at least one metal component selected from Groups 6 to 10 of the Periodic Table of Elements, wherein the catalyst composition exhibits an oxygen chemisorption of greater than 50%. The contacting is conducted under conditions effective to convert at least a portion of the at least one non-aromatic six-membered ring compound in the hydrocarbon stream to benzene and to convert at least a portion of the at least one five-membered ring compound in the hydrocarbon stream to paraffins.Type: ApplicationFiled: December 17, 2010Publication date: October 25, 2012Applicant: ExxonMobil Chemical Patents Inc.Inventors: Tan-Jen Chen, Terry E. Helton, Teng Xu
-
Publication number: 20120271077Abstract: In a dehydrogenation process a hydrocarbon stream comprising at least one non-aromatic six-membered ring compound and at least one five-membered ring compound is contacted with a dehydrogenation catalyst produced by a method comprising treating the support with a liquid composition comprising the dehydrogenation component or a precursor thereof and at least one organic dispersant selected from an amino alcohol and an amino acid. The contacting is conducted under conditions effective to convert at least a portion of the at least one non-aromatic six-membered ring compound in the hydrocarbon stream to benzene and to convert at least a portion of the at least one five-membered ring compound in the hydrocarbon stream to paraffins.Type: ApplicationFiled: December 17, 2010Publication date: October 25, 2012Applicant: Exxonmobile Chemical Patents Inc.Inventors: Teng Xu, Stuart L. Soled, Edward A. Lemon, JR., Christine E. Kliewer, Tan-Jen Chen, Joseph E. Baumgartner, Sabato Miseo
-
Patent number: 8236999Abstract: Presented are one or more aspects and/or one or more embodiments of catalysts, methods of preparation of catalyst, methods of deoxygenation, and methods of fuel production.Type: GrantFiled: December 16, 2011Date of Patent: August 7, 2012Assignee: Energia Technologies, Inc.Inventors: Krishniah Parimi, Thien Duyen Thi Nguyen
-
Publication number: 20100292518Abstract: The invention describes a two-step process for hydrotreatment of a feed derived from a renewable source, comprising: a) a first step, termed a mild pre-hydrogenation step, operating in the presence of a first, metallic, catalyst comprising an active hydrodehydrogenating phase constituted by at least one metal from group VIII and/or at least one metal from group VIB and an amorphous mineral support; and b) a second step, termed the second treatment step, operating in the presence of a second, sulphurized, catalyst comprising an active hydrodehydrogenating phase constituted by at least one non-noble metal from group VIII and/or at least one metal from group VIB and an amorphous mineral support.Type: ApplicationFiled: June 3, 2008Publication date: November 18, 2010Applicant: IFPInventors: Quentin Debuisschert, Jean Cosyns, Thierry Chapus, Damien Hudebine
-
Publication number: 20100137663Abstract: A process for the conversion of lignin to chemical precursors is presented. The process comprises treating the lignin to form less acidic compounds. The process includes reacting lignin with a hydrogenation catalyst under a hydrogen atmosphere to convert acidic oxygenate compounds to less acidic oxygenates or hydrocarbons. The oxygenate compounds are reacted in a dehydrogenation and deoxygenation process to remove the oxygen and to convert the cyclic hydrocarbons back to aromatic compounds.Type: ApplicationFiled: February 27, 2009Publication date: June 3, 2010Inventors: John Q. Chen, Mark B. Koch
-
Publication number: 20100087692Abstract: The present invention provides a hydrogenation method capable of converting cracked kerosene into the raw materials for petrochemical cracking having a high thermal decomposition yield by a hydrogenation reaction. The present invention is a petrochemical process for producing at least any of ethylene, propylene, butane, benzene or toluene by carrying out a thermal decomposition reaction at least using naphtha for the main raw material, wherein cracked kerosene produced from a thermal cracking furnace is hydrogenated using a Pd or Pt catalyst in a two-stage method consisting of a first stage (I), in which a hydrogenation reaction is carried out within the range of 50 to 180° C., and a second stage (II), in which a hydrogenation reaction is carried out within the range of 230 to 350° C., followed by re-supplying all or a portion of these hydrogenated hydrocarbons to a thermal cracking furnace.Type: ApplicationFiled: April 14, 2008Publication date: April 8, 2010Applicant: SHOWA DENKO K.K.Inventors: Yuuji Yoshimura, Makoto Toba, Yasuo Miki, Masako Miki, Shigeru Hatanaka, Tetsuo Kudo, Tetsuo Nakajo
-
Patent number: 7671246Abstract: A catalytic process for converting biomass-derived carbohydrates to liquid alkanes, alkenes, and/or ethers is described. The process uses combinations of self- and crossed-aldol condensation reactions, dehydration reactions, and hydrogenation reactions, over specified metal-containing catalysts, to yield alkane, alkene, and ether products from carbohydrate reactants.Type: GrantFiled: March 5, 2007Date of Patent: March 2, 2010Assignee: Wisconsin Alumni Research FoundationInventors: James A. Dumesic, George W. Huber, Juben N. Chheda, Christopher J. Barrett
-
Patent number: 7651606Abstract: The invention concerns a process for the hydrodesulphurization of gasoline cuts for the production of gasolines with a low sulphur and mercaptans content. Said process comprises at least two hydrodesulphurization steps, HDS1 and HDS2, operated in parallel on two distinct cuts of the gasoline constituting the feed. The flow rate of hydrogen in the hydrodesulphurization step HDS2 is such that the ratio between the flow rate of hydrogen and the flow rate of feed to be treated is less than 80% of the ratio of the flow rates used to desulphurize in the hydrodesulphurization step HDS1.Type: GrantFiled: April 23, 2007Date of Patent: January 26, 2010Assignee: Institut Francais du PetroleInventors: Florent Picard, Quentin Debuisschert, Annick Pucci
-
Patent number: 7514387Abstract: A reformer comprises a housing; a substrate disposed in the housing, wherein the substrate comprises a stabilized aluminate and a stabilized zirconate; and a catalyst disposed on the substrate.Type: GrantFiled: February 15, 2005Date of Patent: April 7, 2009Assignee: Umicore AG & Co. KGInventor: William J. LaBarge
-
Patent number: 7442290Abstract: Mesoporous aluminum oxides with high surface areas have been synthesized using inexpensive, small organic templating agents instead of surfactants. Optionally, some of the aluminum can be framework-substituted by one or more other elements. The material has high thermal stability and possesses a three-dimensionally randomly connected mesopore network with continuously tunable pore sizes. This material can be used as catalysts for dehydration, hydrotreating, hydrogenation, catalytic reforming, steam reforming, amination, Fischer-Tropsch synthesis and Diels-Alder synthesis, etc.Type: GrantFiled: March 21, 2007Date of Patent: October 28, 2008Assignee: Lummus Technology Inc.Inventors: Zhiping Shan, Jacobus Cornelius Jansen, Chuen Y. Yeh, Philip J. Angevine, Thomas Maschmeyer
-
Patent number: 7431828Abstract: A two-stage hydrotreating process is disclosed wherein a hydrocarbon stream is first desulphurized followed by a dehydrogenation step, which process comprises in combination contacting the feed and hydrogen over a hydrotreating catalyst at hydrotreating conditions, heating the hydrotreated effluent and hydrogen-rich gas from the hydrotreating reactor and contacting said effluent and hydrogen gas over a hydrotreating catalyst in a post-treatment reactor at a temperature sufficient to increase the polyaromatic hydrocarbon content and lower the hydrogen content of said effluent.Type: GrantFiled: July 6, 2005Date of Patent: October 7, 2008Assignee: Haldor Topsoe A/SInventors: Michael G. Hunter, Rasmus G. Egeberg, Kim G. Knudsen