Resulting Side-chain Restricted To More Than Five C Atoms, E.g., "detergent Alkylate", Etc. Patents (Class 585/455)
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Patent number: 7566799Abstract: The preparation of alkylaryl compounds takes place, inter alia, by a1) preparation of a C4 -olefin mixture from LPG, LNG or MTO streams, b 1) reaction of the C4-olefin mixture obtained in this way over a metathesis catalyst for the preparation of an olefin mixture comprising 2-pentene and/or 3-hexene, and optional removal of 2-pentene and/or 3-hexene, c1) dimerization of the 2-pentane and/or 3-hexene obtained in stage b1) over a dimerization catalyst to give a mixture comprising C10-12-olefins, and optional removal of the C10-12- olefins, d1) reaction of the C10-12-olefin mixtures obtained in stage a1) with an aromatic hydrocarbon in the presence of an alkylation catalyst to form alkylaromatic compounds, it being possible to add additional linear olefins prior to the reaction.Type: GrantFiled: October 1, 2002Date of Patent: July 28, 2009Assignee: BASF AktiengesellschaftInventors: Ulrich Steinbrenner, Thomas Heidemann, Goetz-Peter Schindler, Juergen Stephan, Heiko Maas
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Patent number: 7541505Abstract: A process for the production of phenyl alkanes by catalytic alkylation on a solid acid catalyst employs at least one moving-bed reactor. This process comprises a catalytic alkylation stage of an aromatic compound by at least one olefin that has 9 to 16 carbon atoms per molecule, combined with a catalyst reactivation circuit. Each reactor contains n reaction zones, whereby each of said zones consists of an acidic solid catalyst, optionally different from one zone to the next. Entering each reaction zone, a fraction of the total amount of olefins necessary to the alkylation reaction is introduced. The phenyl alkanes that are obtained by the process according to the invention are particularly suitable for the production of detergents.Type: GrantFiled: June 8, 2006Date of Patent: June 2, 2009Assignee: Institut Francais du PetroleInventors: Emmanuelle Guillon, Eric Sanchez
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Patent number: 7504548Abstract: The invention relates to a method for formulation of a synthetic gas oil or an additive for gas oil in which an alkyl-aromatic compound or a mixture of alkyl-aromatic compounds is selected based on at least one parameter that is selected from the group that consists of the number of cycles of the aromatic core, the number of alkyl chains that are grafted to the aromatic cycle, the length of the alkyl chain or chains, the position of the aromatic cycle or cycles on the alkyl chain or chains of said alkyl-aromatic compound or compounds such that the cetane number of the synthetic gas oil or the additive for gas oil is greater than 30. The invention also relates to a process for the production of alkyl-aromatic compounds for use as a gas oil or additive.Type: GrantFiled: September 20, 2004Date of Patent: March 17, 2009Assignee: Institut Francais du PetroleInventors: Patrick Briot, Sylvie Lacombe, Jean-François Joly, Eric Llido
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Publication number: 20080194897Abstract: The present disclosure provides a process for selectively producing a desired monoalkylated aromatic compound comprising the step of contacting in a reaction zone an alkylatable aromatic compound with an alkylating agent in the presence of catalyst comprising a porous crystalline material under at least partial liquid phase conditions, said catalyst manufactured from extrudate to comprise catalytic particulate material of from about 125 microns to about 790 microns in size, having an Effectiveness Factor increased from about 25% to about 750% from that of the original extrudate, and having an external surface area to volume ratio of greater than about 79 cm?1.Type: ApplicationFiled: January 25, 2008Publication date: August 14, 2008Inventors: Michael C. Clark, Christine N. Elia, Frederick Y. Lo, Mathew J. Vincent
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Patent number: 7396968Abstract: Processes and apparatus for the alkylation of aromatic compound with mono-olefin aliphatic compound in the presence of solid alkylation catalyst use a lights distillation for obtaining desired selectivities to arylalkane in a energy efficient manner. The processes and apparatus offer the potential for debottlenecking existing arylalkane production facilities and reducing the size and energy requirements for a new arylalkane production facility.Type: GrantFiled: January 25, 2005Date of Patent: July 8, 2008Assignee: UOP LLCInventors: Stephen W. Sohn, Michael R. Smith, Lance A. Baird
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Patent number: 7311815Abstract: A method of preparing high linear paraffin or high end-chain monomethyl content products is accomplished by converting synthesis gas in a Fischer-Tropsch reaction to hydrocarbon products. These may be hydrotreated to provide an n-paraffin content of greater than 50% by weight, with substantially all branched paraffins being monomethyl end-chain branched paraffins. At least one non-linear paraffin isomer, which may be a monomethyl paraffin isomer, may be separated from the hydrocarbon products through distillation to provide an n-paraffin product having an n-paraffin content percentage by weight of the n-paraffin product that is greater than the initial n-paraffin content.Type: GrantFiled: April 30, 2003Date of Patent: December 25, 2007Assignee: Syntroleum CorporationInventor: Armen N. Abazajian
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Patent number: 7297826Abstract: A process is described for producing phenylalkanes by alkylating at least one aromatic compound using at least one linear olefin containing 9 to 16 carbon atoms per molecule. The alkylation reaction is carried out in the presence of at least two different catalysts used in at least two distinct reaction zones. The selectivity for a monoalkylated products of the catalyst contained in the first reaction zone is lower than that for the catalyst contained in the second reaction zone located downstream of the first in the direction movement of the fluids.Type: GrantFiled: November 5, 2002Date of Patent: November 20, 2007Assignee: Institut Francais du PetroleInventors: Jean-François Joly, Patrick Briot
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Patent number: 7297828Abstract: An alkylating process for the production of at least one of 2-, 3-, 4-, 5-, and 6-phenylalkanes by alkylation of an aromatic compound with a feedstock containing at least one olefin comprising at least 9 carbon atoms per molecule, in the presence of a catalyst comprising at least one substrate based on at least a zeolite and a non-zeolitic silica-alumina matrix with a low content of macropores, whereby said matrix contains an amount of more than 5% by weight and less than or equal to 95% by weight of silica (SiO2), whereby said process is carried out at a temperature of between 30 and 400° C., a pressure of between 0.1 and 10 MPa, an hourly volumetric flow rate of 0.50 to 200 h?1, and an aromatic compound/olefin molar ratio of between 1:1 and 50:1.Type: GrantFiled: April 5, 2005Date of Patent: November 20, 2007Assignee: Institut Francais du PetroleInventors: Patrick Euzen, Emmanuelle Guillon
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Patent number: 7282617Abstract: A process for making medium and long chain alkylaromatics and alkylphenols having a high level of anti-Markovnikov addition of the alkyl group. The alkylaromatics and alkylphenols made by the process of the present invention have enhanced stability and are particularly well suited to make highly stable oil additives and enhanced oil recovery surfactants.Type: GrantFiled: March 31, 2006Date of Patent: October 16, 2007Assignee: Chevron U.S.A. Inc.Inventors: William L. Schinski, Curt B. Campbell
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Patent number: 7262333Abstract: The invention relates to a process for the production of at least one compound that is selected from among the 2-, 3-, 4-, 5-, and 6-phenylalkanes by alkylation of an aromatic compound by means of at least one olefin that comprises at least 9 carbon atoms per molecule, in the presence of a catalyst that comprises at least one non-zeolitic substrate with a silicated alumina base that contains an amount of more than 6% by weight and less than or equal to 50% by weight of silica (SiO2) and that exhibits particular characteristics, whereby said process is carried out at a temperature of between 30 and 400° C., a pressure of between 0.1 and 10 MPa, an hourly volumetric flow rate of 0.50 to 200 h?1, and an aromatic compound/olefin molar ratio of between 1:1 and 50:1.Type: GrantFiled: November 5, 2004Date of Patent: August 28, 2007Assignee: Institut Francais du PetroleInventors: Patrick Euzen, Emmanuelle Guillon
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Patent number: 7217850Abstract: The invention relates to a process for the production of phenylalkanes comprising an alkylation reaction of at least one aromatic compound by at least one linear olefin having from 9 to 16 carbon atoms per molecule. Said reaction is carried out in a catalytic reactor in which n reaction zones are present each containing at least one same solid acid catalyst, n being greater than or equal to 2, and at the inlet to each of which at least one fraction of the total quantity of olefins necessary for said reaction is introduced. The phenylalkanes obtained by the process according to the invention are particularly suitable for manufacturing detergents.Type: GrantFiled: May 7, 2004Date of Patent: May 15, 2007Assignee: Institut Francais du PetroleInventors: Emmanuelle Guillon, Eric Sanchez, Patrick Briot
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Patent number: 7183452Abstract: The present invention is directed to novel alkylated aromatic compositions, zeolite catalyst compositions and processes for making the same. The catalyst compositions comprise zeolite Y and mordenite zeolite having a controlled macropore structure. The present invention is also directed to the preparation of the catalyst compositions and their use in the preparation of novel alkylated aromatic compositions. The catalyst compositions of the present invention exhibit reduced deactivation rates during the alkylation process, thereby increasing the life of the catalysts.Type: GrantFiled: February 15, 2006Date of Patent: February 27, 2007Assignees: Chevron Oronite Company LLC, Chevron Oronite S.A.Inventors: Curt B. Campbell, Thomas V. Harris, Pierre Tequi, Jean-Louis Le Coent
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Patent number: 7148388Abstract: In a process for preparing an olefinic hydrocarbon mixture comprising at least 5% by weight of mono-olefin oligomers of the empirical formula: CnH2n where n is greater than or equal to 6, a feedstock comprising n-butene and propylene in a molar ratio of about 1:0.01 to about 1:0.49 is contacted under oligomerization conditions with surface deactivated ZSM-23. The resultant mono-olefin oligomers comprise at least 20 percent by weight of olefins having at least 12 carbon atoms, wherein said olefins having at least 12 carbon atoms have an average of from about 0.8 to about 2.0 C1–C3 alkyl branches per carbon chain.Type: GrantFiled: March 28, 2003Date of Patent: December 12, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Stephen W. Beadle, Cesar M. Cheng-Guajardo, Carolyn B. Duncan, David Wayne Turner, Ramzi Y. Saleh
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Patent number: 7098370Abstract: The invention relates to a process for the production of a mixture of compounds that comprises for the most part at least one mono-alkylbenzene that belongs to the group that is formed by the 2-, 3-, 4-, 5- and 6-phenylalkanes by alkylation of benzene with at least one monoolefin that comprises at least two carbon atoms in its molecule, in the presence of a catalyst that comprises 12-tungstophosphoric acid and/or 12-tungstomolybdic acid, deposited on a substrate that develops a large specific surface area and a high pore volume and that comprises a majority proportion of zirconium oxide (ZrO2).Type: GrantFiled: August 8, 2002Date of Patent: August 29, 2006Assignee: Institut Francais du PetroleInventors: Christine Travers, Jean-Fransois Joly
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Patent number: 7071370Abstract: The present invention is directed to a mordenite zeolite catalyst having a controlled macropore structure. The present invention is also directed to a mordenite zeolite catalyst composite and a process for preparing the catalyst composite. The catalyst composite exhibits reduced deactivation rates during the alkylation process, thereby increasing the life of the catalyst.Type: GrantFiled: July 20, 2005Date of Patent: July 4, 2006Assignees: Chevron Oronite Company LLC, Chevron Oronite S.A.Inventors: Thomas V. Harris, Curt B. Campbell, Pierre Tequi, Jean-Louis Le Coent
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Patent number: 7030285Abstract: A side-chain of a substituted aromatic compound is alkylated by reacting the aromatic compound with an alkylating agent in the presence of a catalyst. The catalyst comprises a restructured smectite clay to which basic ions are incorporated by ion-exchange. The restructuring of the smectite clay is carried out by acid-treating the clay prior to ion-exchange.Type: GrantFiled: January 29, 2001Date of Patent: April 18, 2006Assignee: Optatech CorporationInventors: Adriana De Stefanis, Giorgio Perez, Anthony Tomlinson, Christer Bergst{umlaut over (r)}öm
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Patent number: 6977319Abstract: The present invention is directed to novel alkylated aromatic compositions, zeolite catalyst compositions and processes for making the same. The catalyst compositions comprise zeolite Y and mordenite zeolite having a controlled macropore structure. The present invention is also directed to the preparation of the catalyst compositions and their use in the preparation of novel alkylated aromatic compositions. The catalyst compositions of the present invention exhibit reduced deactivation rates during the alkylation process, thereby increasing the life of the catalysts.Type: GrantFiled: March 12, 2004Date of Patent: December 20, 2005Assignees: Chevron Oronite Company LLC, Chevron Oronite S.A.Inventors: Curt B. Campbell, Thomas V. Harris, Pierre Tequi, Jean-Louis Le Coent
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Patent number: 6762334Abstract: A process for the production of alkylaromatic hydrocarbons by alkylating aromatic hydrocarbons with olefinic hydrocarbons is disclosed. The olefinic hydrocarbons are produced by dehydrogenating paraffinic hydrocarbons. Aromatic byproducts formed in dehydrogenation are removed using an aromatic byproducts removal zone and either a dividing wall distillation column or thermally coupled distillation columns. The process significantly decreases the cost of utilities in producing alkylaromatics, such as precursors for detergent manufacture.Type: GrantFiled: July 9, 2002Date of Patent: July 13, 2004Assignee: UOP LLCInventors: Douglas G. Stewart, Dennis E. O'Brien
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Patent number: 6747182Abstract: A process for preparing alkyl substituted aromatic compounds by alkylating an aromatic compound with an alkylating agent in the presence of a porous crystalline zeolite in which the zeolite has been selectively deluminated to remove nonframework aluminum.Type: GrantFiled: March 20, 2001Date of Patent: June 8, 2004Assignee: ExxonMobil Chemical Patents Inc.Inventors: Hye Kyung C. Timken, Arthur W. Chester, Susan Ardito, Mark P. Hagemeister
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Patent number: 6670516Abstract: A process for producing phenyl-alkanes by paraffin dehydrogenation followed by olefin isomerization and then by alkylation of a phenyl compound by a lightly branched olefin is disclosed. An effluent of the alkylation section comprises paraffins that are recycled to the dehydrogenation step. A process that sulfonates phenyl-alkanes having lightly branched aliphatic alkyl groups to produce modified alkylbenzene sulfonates is also disclosed. In addition, the compositions produced by these processes, which can comprise detergents, lubricants, and lubricant additives, are disclosed.Type: GrantFiled: December 20, 2002Date of Patent: December 30, 2003Assignee: UOP LLCInventors: Richard E. Marinangeli, Leonid B. Galperin, Thomas R. Fritsch, R. Joe Lawson
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Patent number: 6624190Abstract: The invention concerns compounds of formula (I) wherein: A represents R1 or (O)R1 where R1 represents an alkyl group comprising 1 to 30 carbon atoms, linear or branched, saturated or unsaturated, capable of being partly or totally substituted by Hal where Hal represents —Cl,—Br, or —F, and of being interrupted by one or several units selected among —O—,—S—,—C(O)—,—NR3C(O)—, —Ph(R4)n— and —CH2—CH2—O)n′—, wherein R3 represents or —CH2)n″—CH where n″=0 to 17; R4 represents, —CH3,—CH2H5,—C3H7 and n=0 to 4 and n′=1, 2, or 3, or R1 represents a cyclanic radical with diterpene or triterpene root; and R2 represents a C1−C11 linear or branched alkyl group.Type: GrantFiled: May 17, 2001Date of Patent: September 23, 2003Assignee: Universite Pierre et Marie Curie (Paris VI)Inventors: Chadi Khoury, Michel Minier, Francois Le Goffic
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Patent number: 6617481Abstract: The present invention is a process for producing phenyl-alkanes by paraffin adsorptive separation followed by paraffin dehydrogenation and then by alkylation of a phenyl compound by a lightly branched olefin. The adsorptive separation step employs a silicalite adsorbent and, as the desorbent, a C5-C8 linear paraffin, a C5-C8 cycloparaffin, a branched paraffin such as isooctane, or mixtures thereof. The effluent of the alkylation zone comprises paraffins that are recycled to the adsorptive separation step or to the dehydrogenation step. This invention is also a process that sulfonates phenyl-alkanes having lightly branched aliphatic alkyl groups that to produce modified alkylbenzene sulfonates. In addition, this invention is the compositions produced by these processes, which can be used as detergents having improved cleaning effectiveness in hard and/or cold water while also having biodegradability comparable to that of linear alkylbenzene sulfonates, as lubricants, and as lubricant additives.Type: GrantFiled: August 29, 2000Date of Patent: September 9, 2003Assignee: UOP LLCInventors: Santi Kulprathipanja, Richard E. Marinangeli, Stephen W. Sohn, Thomas R. Fritsch, R. Joe Lawson
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Patent number: 6566571Abstract: Process for preparing monofunctional, bifunctional and/or polyfunctional biaryls of the formula (I) Ar—Ar′ (I) by reacting haloaromatics of the formula (II) Ar—X (II) with boron compounds of the formula (IIIa), (IIIb) and/or (IIIc) in the presence of at least one palladium complex of the formula (IVa) or (IVb)Type: GrantFiled: February 4, 2002Date of Patent: May 20, 2003Assignee: Degussa AGInventors: Thomas Riermeier, Matthias Beller, Alexander Zapf
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Patent number: 6525233Abstract: Processes for making particularly branched, especially monomethyl-branched or nongeminal dimethyl-branched surfactants used in cleaning products; preferred processes comprising particular combinations of two or more adsorptive separation steps and, more preferably, particular alkylation steps; products of such processes, including certain modified alkylbenzenes, modified alkylbenzenesulfonate surfactants, and consumer cleaning products, especially laundry detergents, containing them. Preferred processes herein more specifically use specific, unconventional sequences of sorptive separation steps to secure certain branched hydrocarbon fractions which are used in further process steps as alkylating agents for arenes or for other useful surfactant-making purposes. Surprisingly, such fractions can even be derived from effluents from current linear alkylbenzene manufacture.Type: GrantFiled: January 7, 2000Date of Patent: February 25, 2003Assignee: The Procter & Gamble CompanyInventors: Daniel Stedman Connor, Jeffrey John Scheibel, James Charles Theophile Roger Burkett-St. Laurent, Thomas Anthony Cripe, Kevin Lee Kott, Phillip Kyle Vinson
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Patent number: 6521804Abstract: The present invention is a process for producing phenyl-alkanes by alkylation of an aryl compound with an olefinic compound and which uses a mordenite catalyst and a silica-alumina catalyst. This invention is also a process that sulfonates phenyl-alkanes having lightly branched aliphatic alkyl groups to produce modified alkylbenzene sulfonates. In addition, this invention is the compositions produced by these processes, which can be used as detergents having improved cleaning effectiveness in hard and/or cold water while also having biodegradability comparable to that of linear alkylbenzene sulfonates, as lubricants, and as lubricant additives. This invention is moreover the use of compositions produced by these processes as lubricants and lubricant additives.Type: GrantFiled: August 24, 2001Date of Patent: February 18, 2003Assignee: UOP LLCInventors: Richard E. Marinangeli, R. Joe Lawson
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Patent number: 6479720Abstract: A process for the production of alkylaromatic hydrocarbons by alkylating aromatic hydrocarbons with linear olefinic hydrocarbons is disclosed. The linear olefinic hydrocarbons are produced by dehydrogenating linear paraffinic hydrocarbons which are extracted from a heartcut that is distilled from a kerosene boiling range fraction in either a dividing wall fractionation column or in two fully thermally coupled fractionation columns. The process significantly decreases the cost of utilities in producing alkylaromatic precursors for detergent manufacture.Type: GrantFiled: December 29, 1999Date of Patent: November 12, 2002Assignee: UOP LLCInventors: Dennis E. O'Brien, Dennis H. Bielinski, Zhanping Xu
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Patent number: 6429345Abstract: The invention concerns a process for producing at least one compound selected from 2-, 3-, 4-, 5- and 6-phenylalkanes by alkylating benzene using at least one olefin containing at least 9 carbon atoms per molecule, in the presence of a catalyst comprising at least one zeolite with structure type EUO, at least partially in its acid form and at least one matrix, said zeolite comprising silicon and at least one element T selected from the group formed by aluminium, iron, gallium and boron (preferably aluminium and boron), with an Si/T atomic ratio of more than 5; said process being carried out at a temperature in the range 30° C. to 400° C., a pressure in the range 0.1 to 10 MPa, with an hourly space velocity of 0.50 to 200 h−1, and a benzene/olefins mole ratio in the range 1:1 to 50:1.Type: GrantFiled: June 22, 2000Date of Patent: August 6, 2002Assignee: Institut Francais du PetroleInventors: Jean-François Joly, Fabio Alario, Elisabeth Merlen, Julia Magne-Drisch
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Patent number: 6417420Abstract: A process for the production of alkylaromatic hydrocarbons by alkylating aromatic hydrocarbons with olefinic hydrocarbons is disclosed. The olefinic hydrocarbons are produced by dehydrogenating paraffinic hydrocarbons. Aromatic byproducts formed in dehydrogenation are removed using an aromatic byproducts removal zone and either a dividing wall distillation column or thermally coupled distillation columns. The process significantly decreases the cost of utilities in producing alkylaromatics, such as precursors for detergent manufacture.Type: GrantFiled: February 26, 2001Date of Patent: July 9, 2002Assignee: UOP LLCInventors: Douglas G. Stewart, Dennis E. O'Brien
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Publication number: 20020049359Abstract: A process for preparing alkyl substituted aromatic compounds by alkylating an aromatic compound with an alkylating agent in the presence of a porous crystalline zeolite in which the zeolite has been selectively deluminated to remove nonframework aluminum.Type: ApplicationFiled: March 20, 2001Publication date: April 25, 2002Inventors: Hye Kyung C. Timken, Arthur W. Chester, Susan Ardito, Mark P. Hagemeister
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Patent number: 6350930Abstract: A method for producing an aromatic compound styrenic compound adduct comprising the steps of: (1) reacting an aromatic compound and a styrenic compound in a first reactor 1 of fixed-bed flow type in a liquid phase in the presence of a solid acid catalyst, (2) circulating a part of the reaction mixture from the above step to the first reactor 1, (3) feeding a reaction mixture flowing out from the first reactor to a second reactor 3, thereby reducing the content of unsaturated components with the aid of a solid acid catalyst, and (4) distilling the resultant reaction mixture, to thereby obtain a fraction having a reduced content of unsaturated components. The method can be used for producing an aromatic compound/styrenic compound adduct having a reduced content of unsaturated components in high yield and at a low cost.Type: GrantFiled: April 19, 2000Date of Patent: February 26, 2002Assignee: Nippon Petrochemicals Company, LimitedInventors: Hideyuki Dohi, Shozo Hayashi
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Patent number: 6262325Abstract: The catalyst comprises at least one alkali metal on a support which has the general formula (I) An′Tim′Zrp′Hfq′On′+2(m′+p′+q′) (I) where A is a divalent metal, 20·(m′+p′+q′)>n′>0.05·(m′+p′+q′), and which may be doped with at least one compound of an alkali metal and/or alkaline earth metal, where the alkali metal/support ratio by weight is 0.01-5:1 and, when a dopant is present, the dopant/support ratio by weight is 0.01-5:1, and where the proportion of support phase corresponding to the ZrO2 structure or an alkaline earth metal oxide structure or consisting of ZrO2 or alkaline earth metal oxide is less than 10% by weight.Type: GrantFiled: October 6, 1999Date of Patent: July 17, 2001Assignee: BASF AktiengessellschaftInventors: Thomas Narbeshuber, Ulrich Steinbrenner
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Patent number: 6255549Abstract: A fraction of low bromine number mainly containing a styrenic compound/aromatic compound adduct can be attained, by feeding reaction materials of a styrenic compound and an aromatic compound to a fixed-bed flow reactor packed with a solid acid catalyst in a liquid phase at a temperature in the range of 40 to 350° C. to form a styrenic compound/aromatic compound adduct, in which (1) the feed of reaction materials is stopped when the bromine number of the above fraction is increased up to a predetermined value, (2) a saturated aromatic hydrocarbon having a mean value of the proportion of aromatic ring carbons in a molecule of 55% or more is fed to the reactor in a liquid phase at a temperature higher by 5 to 150° C. than that of the reaction mixture just before the above stopping, and (3) the feed of reaction materials is then restarted to obtain the fraction.Type: GrantFiled: April 19, 2000Date of Patent: July 3, 2001Assignee: Nippon Petrochemicals Company, LimitedInventors: Hideyuki Dohi, Shozo Hayashi
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Patent number: 6225516Abstract: Process for the production of linear alkylaromatic hydrocarbons comprising: a) dehydrogenating C10-C14 n-paraffins; b) selectively hydrogenating the diolefins produced during step (a); c) feeding stream (b) and an aromatic hydrocarbon to an alkylation unit; d) distilling the alkylated stream into its main constituents; e) subjecting a paraffinic stream containing aromatic by-products, leaving step (d), to a hydrogenation step; f) recycling the stream leaving step (e) to the dehydrogenation unit of step (a).Type: GrantFiled: July 15, 1999Date of Patent: May 1, 2001Assignee: Condea Augusta S.p.A.Inventors: Pierino Radici, Pierluigi Cozzi, Rosanna Ontano, Agostino Zatta
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Patent number: 6187981Abstract: The present invention is a process for producing aryl-alkanes by paraffin isomerization followed by paraffin dehydrogenation and then by alkylation of an aryl compound by a lightly branched olefin. The effluent of the alkylation zone comprises paraffins that are recycled to the isomerization step or to the dehydrogenation step. This invention is also a process that that sulfonates phenyl-alkanes having lightly branched aliphatic alkyl groups that to produce modified alkylbenzene sulfonates. In addition, this invention is the compositions produced by these processes, which can be used as detergents having improved cleaning effectiveness in hard and/or cold water while also having biodegradability comparable to that of linear alkylbenzene sulfonates, as lubricants, and as lubricant additives. This invention is moreover the use of compositions produced by these processes as lubricants and lubricant additives.Type: GrantFiled: July 19, 1999Date of Patent: February 13, 2001Assignee: UOP LLCInventors: Richard E. Marinangeli, R. Joe Lawson, Leonid B. Galperin, Thomas R. Fritsch
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Patent number: 6169219Abstract: Detergent-quality linear alkylaromatics are recovered from an alkylation reactor effluent containing polymeric byproducts, such as dimers and trimers of the olefinic feedstock. The effluent stream passes to another reactor operating at a higher temperature than the first reactor. Heavy alkylate is separated from the detergent-quality linear alkylaromatics by conventional separation methods such as distillation. This invention decreases the concentration of polymeric byproducts in the linear alkylaromatics. The benefits of this invention include a higher linearity and/or a lower bromine index in the detergent-quality linear alkylaromatic product, as well as a lower color after sulfonation of the linear alkylbenzene sulfonate.Type: GrantFiled: June 9, 1999Date of Patent: January 2, 2001Assignee: UOP LLCInventors: Masami Kojima, Thomas R. Fritsch, Kurt A. Detrick
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Patent number: 6166281Abstract: This invention is directed to a fluorine-containing mordenite catalyst and use thereof in the manufacture of linear alkylbenzene (LAB) by alkylation of benzene with an olefin. The paraffin may have from about 10 to 14 carbons. The fluorine-containing mordenite is prepared typically by treatment with an aqueous hydrogen fluoride solution. The benzene alkylation may be conducted using reactive distillation. This invention is also directed to a process for production of LAB having a high 2-phenyl isomer content by combining LAB product from the fluorine-containing mordenite product from a conventional LAB alkylation catalyst such as hydrogen fluoride.Type: GrantFiled: October 19, 1998Date of Patent: December 26, 2000Assignee: Huntsman Petrochemical CorporationInventor: Prakasa Rao Anantaneni
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Patent number: 6156552Abstract: The invention provides variant lipases with improved washing performance, including good performance in washing with a detergent having a high content of anionic surfactant at low washing temperature at a short washing time. More particularly, the invention relates to variants of the wild-type lipase from Pseudomonas sp. strain SD 705, deposited as FERM BP-4772.Type: GrantFiled: February 17, 1999Date of Patent: December 5, 2000Assignee: Novo Nordisk A/SInventors: Jens Sigurd Okkels, Shiro Fukuyama, Tomoko Matsui, Tadashi Yoneda
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Patent number: 6137020Abstract: A process for reducing the amount of undesirable byproducts, for example multi-ring compounds known as heavy residue in a process for the alkylation of an aromatic hydrocarbon with an olefin using a silicalite catalyst is disclosed. The process comprises supplying a feedstock containing benzene to a reaction zone with an alkylating agent in a molar ratio of benzene to alkylating agent of from about 2:1 to about 20:1 and into contact with an aluminosilicate alkylation catalyst having an average crystallite size of less than about 0.50 .mu.m and wherein the size of about 90% of the crystallites is less than 0.70 .mu.m. The catalyst is characterized by an Si/Al atomic ratio in the range from between 50 and 150 and a maximum pore size in the range from about 1000 to 1800 .ANG.. The catalyst has a sodium content of less than about 50 ppm and the reaction is carried out under conversion conditions including a temperature of from about 250.degree. C. to about 550.degree. C.Type: GrantFiled: July 31, 1998Date of Patent: October 24, 2000Assignee: Fina Technology, Inc.Inventors: James R. Butler, Mark E. Kuchenmeister
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Patent number: 6133492Abstract: This invention is directed to a fluorine-containing mordenite catalyst and use thereof in the manufacture of linear alkylbenzene (LAB) by alkylation of benzene with an olefin. The olefin may have from about 10 to 14 carbons. The fluorine-containing mordenite is prepared typically by treatment with an aqueous hydrogen fluoride solution. The benzene alkylation may be conducted using reactive distillation. This invention is also directed to a process for production of LAB having a high 2-phenyl isomer content by use of the fluorine-containing mordenite in conjunction with a conventional solid LAB alkylation catalyst. The two catalysts may be used in a mixed catalyst bed or may be packed in series, with the relative proportions being adjusted to provide a desired 2-phenyl isomer content of in the final product.Type: GrantFiled: October 19, 1998Date of Patent: October 17, 2000Assignee: Huntsman Petrochemical CorporationInventor: Prakasa Rao Anantaneni
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Patent number: 6111158Abstract: The present invention is a process for producing phenyl-alkanes at alkylation conditions in the presence of a zeolite having an NES zeolite structure type, such as NU-87. This invention produces phenyl-alkanes having lightly branched aliphatic alkyl groups which are used to produce modified alkylbenzene sulfonates that have improved cleaning effectiveness in hard and/or cold water while also having biodegradability comparable to that of linear alkylbenzene sulfonates.Type: GrantFiled: March 4, 1999Date of Patent: August 29, 2000Assignee: UOP LLCInventors: Richard E. Marinangeli, Michael G. Gatter, R. Joe Lawson, Thomas R. Fritsch
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Patent number: 6069285Abstract: An integrated alkylaromatic process using a solid alkylation catalyst and an aromatic rectifier is disclosed for alkylating aromatics with olefins and for regenerating the solid alkylation catalyst. The aromatic rectifier produces a relatively low-purity aromatic-containing overhead stream that is used in producing alkylaromatics, and an aromatic column produces a relatively high-purity aromatic-containing overhead stream that is used in regenerating the solid alkylation catalyst. In another embodiment, this process is further integrated with a paraffin dehydrogenation zone and an aromatic by-products removal zone. This invention produces the benzene-containing streams that are necessary for alkylating and for regenerating in a more economical manner than prior art processes.Type: GrantFiled: June 9, 1999Date of Patent: May 30, 2000Assignee: UOP LLCInventors: Thomas R. Fritsch, Steven F. Eshelman, Dennis E. O'Brien
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Patent number: 6037513Abstract: There is described a process and a catalyst for the hydroalkylation of an aromatic hydrocarbon, particularly benzene, wherein the catalyst comprises a first metal having hydrogenation activity and a crystalline inorganic oxide material having a X-ray diffraction pattern including the following d-spacing maxima 12.4.+-.0.25, 6.9.+-.0.15, 3.57.+-.0.07 and 3.42.+-.0.07.Type: GrantFiled: July 9, 1998Date of Patent: March 14, 2000Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, Jane C. Cheng, Terry E. Helton, Michael A. Steckel, Scott A. Stevenson
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Patent number: 5977424Abstract: A catalyst is disclosed which comprises a clay belonging to the family of smectites, containing multi-metal pillars, together with a process which uses such a catalyst for the alkylation of aromatic hydrocarbons by means of long chain linear olefins. The resulting alkyl-aromatic compounds are useful for preparing biodegradable synthetic detergents.Type: GrantFiled: April 23, 1998Date of Patent: November 2, 1999Assignee: Enichem Augusta S.p.A.Inventors: Giovanni Colombo, Stefano Amarilli, Imre Kiricsi, Carlo Perego
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Patent number: 5922922Abstract: An alkylated aromatic hydrocarbon is produced having the following properties: (a) less than 40 wt. % of the alkylated aromatic hydrocarbon is 2-aryl; and (b) at least 20 wt. % of the alkylated aromatic hydrocarbon is a monoalkylate. That alkylated aromatic hydrocarbon is produced by isomerizing a normal alpha-olefin having from 20 to 28 carbon atoms in the presence of a first acidic catalyst to produce a partially-branched, isomerized olefin, then either benzene or toluene is alkylated with the partially-branched, isomerized olefin in the presence of a second solid, acidic catalyst. The first acidic catalyst can be a molecular sieve with a one-dimensional pore system. The second acidic catalyst can be a zeolite Y having a silica to alumina ratio of at least 40:1.Type: GrantFiled: July 17, 1997Date of Patent: July 13, 1999Assignee: Chevron Chemical CompanyInventors: Thomas V. Harris, Curt B. Campbell, Mohammed M. Habib
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Patent number: 5824832Abstract: A low temperature molten ionic liquid composition comprising a mixture of a metal halide and an alkyl-containing amine hydrohalide salt can be used in linear alkylbenzene formation. The metal halide is a covalently bonded metal halide which can contain a metal selected from the group comprised of aluminum, gallium, iron, copper, zinc, and indium, and is most preferably aluminum trichloride. The alkyl-containing amine hydrohalide salt may contain up to three alkyl groups, which are preferably lower alkyl, such as methyl and ethyl.Type: GrantFiled: March 27, 1997Date of Patent: October 20, 1998Assignee: Akzo Nobel NVInventors: Fawzy G. Sherif, Lieh-Jiun Shyu, Carl C. Greco
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Patent number: 5705724Abstract: A process is disclosed for the production of alkylaromatic compounds employing olefinic liquid from thermally or catalytically cracked plastics as alkylating agent. The process comprises contacting a feedstream comprising alkylatable aromatics and the olefinic liquid with acidic alkylation catalyst under alkylation conditions in an alkylation zone; and recovering an effluent stream comprising alkylaromatic compounds. The alkylation can be performed with the product of plastics pyrolysis or with non-degraded plastic feedstock in-situ with thermal/catalytic degradation of the plastic.Type: GrantFiled: October 26, 1995Date of Patent: January 6, 1998Assignee: Mobil Oil CorporationInventors: Nick A. Collins, Larry A. Green, Anagha A. Gupte, David O. Marler, William J. Tracy, III
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Patent number: 5629463Abstract: Long chain alkyl substituted naphthalenes are produced by alkylating naphthalene with an olefin or other alkylating agent with at least 6, and usually 12 to 20 carbon atoms, in the presence of an alkylation catalyst comprising a zeolite having rare earth cations, and both ammonium and protonic species, associated with the exchangeable sites of the zeolite. The zeolite is usually a large pore size zeolite such as USY. The presence of rare earths and both ammonium and protonic species increases selectivity for production of long chain mono-alkyl substituted naphthalenes in preference to more highly substituted products.Type: GrantFiled: August 25, 1995Date of Patent: May 13, 1997Assignee: Mobil Oil CorporationInventors: Susan C. Ardito, Henry Ashjian, Thomas F. Degnan, Terry E. Helton, Quang N. Le, Augusto R. Quinones
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Patent number: 5625102Abstract: A method of alkylating the side chain of alkyl-substituted aromatic hydrocarbons. The method comprises the steps of thermally treating an alumina by calcining in air and then degassing under vacuum to prepare an alumina carrier, loading an alkali metal on the alumina carrier by an impregnation method using the alkali metal dissolved in liquid ammonia, thermally treating the alkali metal loaded alumina carrier under vacuum to prepare a catalyst, then reacting an alkyl-substituted aromatic hydrocarbon with an aliphatic monoolefin, using the catalyst, under an atmosphere substantially free of oxygen, water and carbon dioxide gas to alkylate the side chain of the alkyl-substituted aromatic hydrocarbon.Type: GrantFiled: December 27, 1994Date of Patent: April 29, 1997Assignee: Mitsubishi Oil Co., Ltd.Inventors: Takaya Matsumoto, Yoshiichi Kumagai, Fumio Kumata
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Patent number: 5574198Abstract: The present invention relates to an improved process for preparing linear alkylbenzenes falling within such range as used in detergency (C.sub.10 -C.sub.14), which process consists of alkylating aromatic hydrocarbons (above all, benzene) with n-olefins in the presence of AlCl.sub.3, wherein said n-olefins are obtained by dehydrogenating n-paraffins.Type: GrantFiled: April 10, 1995Date of Patent: November 12, 1996Assignee: Enichem Augusta S.p.A.Inventors: Pierino Radici, Pierluigi Cozzi, Giuseppe Giuffrida, Agostino Zatta
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Patent number: 5488193Abstract: A process for reducing the mutagenicity of a polynuclear aromatic containing material containing from three to seven fused aromatic rings, especially a hydrocarbon refinery stream. The process reduces the initial mutagenicity index to a lower value by alkylating the compound with an alkylating agent which introduces an alkyl substituent having from three to five carbon atoms into the aromatic compound in the presence of an acid catalyst under alkylation conditions.Type: GrantFiled: January 25, 1995Date of Patent: January 30, 1996Assignee: Mobil Oil CorporationInventors: Carl R. Mackerer, Timothy A. Roy, Gary R. Blackburn