Patents Assigned to Badger Licensing, LLC
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Patent number: 11760710Abstract: A method is disclosed for treating a residual stream from bisphenol manufacture, wherein the residual stream comprises unreacted phenols, bisphenol isomers, trisphenols, organic sulfides and water. The method comprises contacting at least a portion of the residual stream or a reaction product thereof with an acidic catalyst under conditions sufficient to allow acid-catalyzed hydrolysis of organic sulfides in the residual stream to the corresponding thiols and produce an effluent stream, and then distilling at least a portion of the effluent stream to recover distillate products comprising phenols and thiols and produce a bottoms product comprising bisphenol isomers and trisphenols, and having a lower content of organic sulfides than the residual stream.Type: GrantFiled: July 6, 2018Date of Patent: September 19, 2023Assignee: BADGER LICENSING LLCInventor: David Palmer
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Patent number: 11260378Abstract: A catalyst system useful in the production of bisphenol-A comprises (a) an acidic heterogeneous catalyst; (b) a first catalyst promoter comprising at least one organic sulfur-containing compound; and (c) a second catalyst promoter different from the first catalyst promoter and comprising at least one organic Brønsted acidic ionic compound.Type: GrantFiled: April 18, 2018Date of Patent: March 1, 2022Assignee: BADGER LICENSING LLCInventor: Christopher Papile
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Patent number: 10995284Abstract: A process is described for reducing the level of benzene in a refinery gasoline feed containing benzene and at least one C5+ olefin, in which the refinery gasoline feed is contacted with a first alkylation catalyst under conditions effective to react at least part of the C5+ olefin and benzene in the refinery gasoline feed and produce a first alkylation effluent. The first alkylation effluent is separated into at least (i) a first fraction rich in benzene, (ii) a second fraction rich in C7 to C12 hydrocarbons and (iii) a third fraction rich in C13+ hydrocarbons. At least part of the first fraction is contacted with an alkylating agent comprising one or more C2 to C4 olefins in the presence of a second alkylation catalyst under conditions effective to produce a second alkylation effluent which has reduced benzene content as compared with the first fraction.Type: GrantFiled: April 26, 2016Date of Patent: May 4, 2021Assignee: BADGER LICENSING LLCInventor: Shyh-Yuan H. Hwang
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Patent number: 10899683Abstract: A process for producing ethylbenzene is described in which benzene and ethylene are supplied to an alkylation reaction zone. Also added to the alkylation reaction zone is a C3+ olefin in an amount of at least 200 ppm by weight of the ethylene supplied to the alkylation reaction zone. The benzene, ethylene and C3+ olefin are contacted with an alkylation catalyst in the alkylation reaction zone to alkylate at least part of the benzene and produce an alkylation effluent comprising ethylbenzene, polyethylated benzene and at least one mono-C3+ alkyl benzene. The alkylation effluent is separated into a first product fraction comprising ethylbenzene and a second fraction comprising polyethylated benzene and the at least one mono-C3+ alkyl benzene. The second fraction is then contacted with benzene in the presence of a transalkylation catalyst to convert at least part of the polyethylated benzene to ethylbenzene and produce a transalkylation effluent.Type: GrantFiled: February 17, 2016Date of Patent: January 26, 2021Assignee: BADGER LICENSING LLCInventors: Brian Maerz, Chung-Ming Chi, Raghavender Bhoomi
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Publication number: 20200047170Abstract: A catalyst system useful in the production of bisphenol-A comprises (a) an acidic heterogeneous catalyst; (b) a first catalyst promoter comprising at least one organic sulfur-containing compound; and (c) a second catalyst promoter different from the first catalyst promoter and comprising at least one organic Brønsted acidic ionic compound.Type: ApplicationFiled: April 18, 2018Publication date: February 13, 2020Applicant: BADGER LICENSING LLCInventor: Christopher Papile
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Patent number: 10343956Abstract: In a method for producing a monoalkylated aromatic product, benzene and an alkylating agent are contacted with an alkylation catalyst in a first alkylation reaction zone under alkylation conditions to produce a first alkylation effluent comprising the monoalkylated aromatic product, polyalkylated aromatic product, unreacted benzene and C5, C6 and/or C7 non-aromatic compounds. A purge stream containing C5, C6 and/or C7 non-aromatic compounds and unreacted benzene is removed from the first alkylation effluent and is contacted with an alkylating agent in a second alkylation reaction zone in the presence of an alkylation catalyst under alkylation conditions to produce a second alkylation effluent comprising monoalkylated aromatic product, polyalkylated aromatic product and C5, C6 and/or C7 non-aromatic compounds.Type: GrantFiled: October 15, 2015Date of Patent: July 9, 2019Assignee: BADGER LICENSING LLCInventor: Slawomir J. Oleksy
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Patent number: 10280128Abstract: In a process for alkylating an aromatic hydrocarbon feedstock with an olefin feedstock, at least one of the aromatic hydrocarbon and olefin feedstocks is passed through a pretreatment unit containing an adsorbent such that the adsorbent removes impurities contained by the feedstock. Passage of the at least one feedstock through the pretreatment unit is then terminated and a heated inert gas is passed through the pretreatment unit such that the inert gas desorbs impurities from the adsorbent to produce an inert gas effluent stream containing the desorbed impurities. A condensable fluid is added to at least part of the inert gas effluent stream such that at least a portion of the impurities contained therein condense with said fluid to leave a purified inert gas stream, which is recycled to the pretreatment unit.Type: GrantFiled: July 25, 2013Date of Patent: May 7, 2019Assignee: BADGER LICENSING LLCInventors: Brian Maerz, Douglas Hubbell, Maruti Bhandarkar, Vijay Nanda
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Patent number: 10260012Abstract: In a process for reducing the level of benzene in a refinery gasoline feed containing benzene and at least one C4+ olefin, the feed is contacted with a first alkylation catalyst under conditions effective to react at least part of the C4+ olefin and benzene in the refinery gasoline feed and produce a first effluent containing C10+ hydrocarbons. At least part of the C10+ hydrocarbons is removed from the first effluent to produce a second effluent, which is then contacted with an alkylating agent selected from one or more C2 to C5 olefins in the presence of a second alkylation catalyst to produce a third effluent which has reduced benzene content as compared with the second effluent.Type: GrantFiled: November 24, 2015Date of Patent: April 16, 2019Assignee: BADGER LICENSING LLCInventors: Shyh-Yuan Henry Hwang, Erik J. Moy
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Publication number: 20190016647Abstract: A process for producing ethylbenzene is described in which benzene and ethylene are supplied to an alkylation reaction zone. Also added to the alkylation reaction zone is a C3+ olefin in an amount of at least 200 ppm by weight of the ethylene supplied to the alkylation reaction zone. The benzene, ethylene and C3+ olefin are contacted with an alkylation catalyst in the alkylation reaction zone to alkylate at least part of the benzene and produce an alkylation effluent comprising ethylbenzene, polyethylated benzene and at least one mono-C3+ alkyl benzene. The alkylation effluent is separated into a first product fraction comprising ethylbenzene and a second fraction comprising polyethylated benzene and the at least one mono-C3+ alkyl benzene. The second fraction is then contacted with benzene in the presence of a transalkylation catalyst to convert at least part of the polyethylated benzene to ethylbenzene and produce a transalkylation effluent.Type: ApplicationFiled: February 17, 2016Publication date: January 17, 2019Applicant: Badger Licensing LLCInventors: Brian MAERZ, Chung-Ming CHI, Raghavender BHOOMI
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Patent number: 10138180Abstract: In a process for producing styrene, benzene is alkylated with ethylene to produce ethylbenzene and at least some of the ethylbenzene is dehydrogenated to produce styrene, together with benzene and toluene as by-products. At least part of the benzene by-product is passed through a bed of an adsorbent comprising at least one of an acidic clay, alumina, an acidic ion exchange resin and an acidic molecular sieve to remove basic nitrogenous impurities therefrom and produce a purified benzene by-product, which is then recycled to the alkylation step.Type: GrantFiled: November 27, 2012Date of Patent: November 27, 2018Assignee: BADGER LICENSING LLCInventors: Brian Maerz, Vijay Nanda, Maruti Bhandarkar, Matthew Vincent
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Patent number: 9850187Abstract: A process is described for producing cumene comprising contacting benzene and a C3 alkylating agent under alkylation conditions with an alkylation catalyst in an alkylation zone to produce an alkylation effluent comprising cumene and alkylaromatic compounds heavier than cumene. Cumene is recovered from the alkylation effluent to leave a byproduct stream containing the alkylaromatic compounds heavier than cumene, which is separated into a polyisopropylbenzene-containing stream, an aromatic overhead stream, and a bottoms product. At least part of the aromatic overhead stream is recycled to the alkylation zone to reduce raw material consumption and improve cumene yield.Type: GrantFiled: June 27, 2012Date of Patent: December 26, 2017Assignee: BADGER LICENSING LLCInventors: Shyh-Yuan H. Hwang, Dana E. Johnson
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Patent number: 9834493Abstract: A process for reducing the benzene content of gasoline stream, such as a reformate or light naphtha, comprises alkylating the gasoline stream in a reaction zone with an olefin alkylating agent. A paraffinic stream comprising C5 to ClO paraffins is fed to the inlet of the alkylation reaction zone.Type: GrantFiled: February 7, 2011Date of Patent: December 5, 2017Assignee: BADGER LICENSING LLCInventors: Shyh-Yuan H. Hwang, Ronald Birkhoff, Richard F. Guarino, J. Erik Moy, Geeta Pherwani
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Patent number: 9796644Abstract: An integrated process for producing cumene and purifying isopropanol is described, in which a crude isopropanol stream containing in excess of 0.1 wt % water is separated into a dry isopropanol fraction containing no more than 0.1 wt % water and a wet isopropanol fraction containing the remainder of the water in said crude isopropanol stream. The dry isopropanol fraction is recovered and the wet isopropanol fraction is contacted with benzene in an alkylation zone under alkylation conditions such that at least part of the isopropanol reacts with the benzene to produce an effluent stream comprising cumene.Type: GrantFiled: August 14, 2012Date of Patent: October 24, 2017Assignee: BADGER LICENSING LLCInventors: Ronald Birkhoff, Raghavender Bhoomi
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Patent number: 9476831Abstract: A process for producing an alkylated aromatic product in a reactor by reacting an alkylatable aromatic compound feedstock with another feedstock comprising alkene component and alkane component in a reaction zone containing an alkylation catalyst. The reaction zone is operated in predominantly liquid phase without inter-zone alkane removal. The polyalkylated aromatic compounds can be separated as feed stream for transalkylation reaction in a transalkylation reaction zone.Type: GrantFiled: March 7, 2011Date of Patent: October 25, 2016Assignee: BADGER LICENSING LLCInventors: Michael C. Clark, Brian Maerz
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Patent number: 9259722Abstract: In a process for producing cumene, benzene and a C3 alkylating agent comprising isopropanol are supplied to an alkylation zone comprising a molecular sieve alkylation catalyst under alkylation conditions such that the isopropanol reacts with the benzene to produce a reaction product comprising cumene. Subsequently, the supply of benzene and C3 alkylating agent to the alkylation zone is ceased and a gaseous stripping agent is supplied to the molecular sieve alkylation catalyst under conditions effective to remove nitrogenous impurities deposited on the catalyst during the preceding alkylation reaction. The supply of benzene and C3 alkylating agent to the alkylation zone is then reinitiated.Type: GrantFiled: July 23, 2013Date of Patent: February 16, 2016Assignee: BADGER LICENSING LLCInventors: Ronald Birkhoff, Shyh-Yuan H. Hwang
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Patent number: 9255053Abstract: In a method of treating a residue stream from the production of bisphenol-A, the residue stream is contacted with an aqueous solution of a base under conditions effective to hydrolyze at least part of said residue stream into acetone and phenol and produce an effluent stream. Acetone is recovered from the effluent stream to produce a phenol-containing mixed phase stream which is substantially free of acetone and which contains water and unhydrolyzed heavy organic compounds. The phenol-containing mixed phase stream is then treated with a water-immiscible organic solvent to extract phenol and unhydrolyzed heavy organic compounds into said solvent and produce an organic phase containing the solvent, phenol and unhydrolyzed heavy aromatic compounds and an aqueous phase with reduced concentrations of phenol and unhydrolyzed heavy organic compounds. At least part of the phenol and the organic solvent are subsequently recovered from the organic phase.Type: GrantFiled: June 4, 2012Date of Patent: February 9, 2016Assignee: BADGER LICENSING LLCInventors: David P. Palmer, Steven D. Evitt, Stephen W. Fetsko, Chung-Ming Chi
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Patent number: 9221736Abstract: In a process for producing phenol, benzene is contacted with a C3 alkylating agent comprising isopropanol under alkylation conditions such that at least part of the isopropanol reacts with the benzene to produce cumene. At least part of the resultant cumene is then oxidized in the presence of an oxidizing gas to produce an oxidation effluent comprising cumene hydroperoxide, unreacted cumene and a spent oxidizing gas. The unreacted cumene is separated from the oxidation effluent and is treated to remove nitrogenous impurities therefrom and produce a purified cumene stream, which is recycled to the oxidization step. At least part of the cumene hydroperoxide from the oxidation effluent is cleaved to produce a cleavage effluent comprising phenol and acetone. The phenol is recovered phenol from the cleavage effluent, whereas at least part of the acetone from the cleavage effluent is hydrogenated to produce isopropanol for recycle to the alkylation step.Type: GrantFiled: June 17, 2013Date of Patent: December 29, 2015Assignee: BADGER LICENSING LLCInventor: Ronald Birkhoff
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Patent number: 9212107Abstract: In a process for producing cumene, isopropanol containing nitrogenous impurities is reacted with benzene in an alkylation reactor to produce an effluent stream comprising cumene, unreacted benzene and water. Water is removed from the effluent stream and an aliquot of the resultant dried effluent stream is treated to remove nitrogenous impurities and produce a purified recycle stream. At least part of the purified recycle stream is then recycled to the alkylation reactor. In an alternative embodiment, the isopropanol is combined with fresh and/or recycled benzene and the combined stream is treated to remove nitrogenous impurities before being fed to the alkylation reactor.Type: GrantFiled: July 2, 2013Date of Patent: December 15, 2015Assignee: BADGER LICENSING LLCInventors: Ronald Birkhoff, Shyh-Yuan H. Hwang
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Patent number: 9200215Abstract: In a process for alkylating benzene contained in a benzene-containing refinery gasoline stream, the benzene-containing refinery gasoline stream is contacted with an alkylating agent selected from one or more C2 to C5 olefins in at least one alkylation reaction zone under alkylation conditions to produce an alkylated effluent which has reduced benzene content as compared with said refinery gasoline stream and is essentially free of said alkylating agent. An aliquot of the alkylated effluent is then recycled to the one at least one alkylation reaction zone such that the molar ratio of alkylatable aromatic compounds to said alkylating agent in the combined refinery gasoline and recycle streams introduced into the at least one alkylation reaction zone is at least 1.0:1.Type: GrantFiled: November 30, 2011Date of Patent: December 1, 2015Assignee: BADGER LICENSING LLCInventors: Shyh-Yuan H. Hwang, Ronald Birkhoff, Richard F. Guarino, J. Erik Moy, Joseph C. Peters
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Patent number: 9199891Abstract: A process is disclosed for alkylating benzene contained in a benzene-containing refinery gasoline stream also comprising at least 0.1 wt % of at least one C6 to C8 olefin. In the process, the refinery gasoline stream is contacted under alkylation conditions with an alkylating agent selected from one or more C2 to C5 olefins in at least a first alkylation reaction zone and a second alkylation reaction zone connected in series to produce an alkylated effluent, which has reduced benzene content as compared with said refinery gasoline stream. All of the refinery gasoline stream is introduced into the first alkylation reaction stage, whereas an aliquot of the alkylated effluent is recycled and introduced to the second, but not the first, alkylation reaction zone.Type: GrantFiled: November 30, 2011Date of Patent: December 1, 2015Assignee: BADGER LICENSING LLCInventors: Shyh-Yuan H. Hwang, Ronald Birkhoff, Richard F. Guarino, J. Erik Moy, Joseph C. Peters