Definite Molecular Weight Product, E.g., Dimer, Etc. Patents (Class 585/510)
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Patent number: 6284938Abstract: A process for the production of C8 and higher carbon number alkene oligomers by the oligomerization of light olefins to heavier olefins is improved by the addition of heavy paraffins to the oligomerization zone. The recycle of the heavy paraffins extends the catalyst activity and improves the catalyst life. The non-reactive paraffin stream may be recycled through the process with minimal losses and make-up.Type: GrantFiled: December 20, 1999Date of Patent: September 4, 2001Assignee: UOP LLCInventors: Laurence O. Stine, Brian S. Muldoon, Steven C. Gimre, Robert R. Frame
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Patent number: 6281401Abstract: A process for oligomerizing at least one heavy olefin having at least 5 carbon atoms per molecule in the presence of at least one co-fed light olefin having less than 5 carbon atoms per molecule is disclosed. The presence of the at least one co-fed light olefin results in increased C6=(C6 olefin) conversion (if present as one of the at least one heavy olefins), increased weight % of C11+ hydrocarbons in the C9+ material of the product and increased cetane of the C9+ material of the product as compared to the oligomerization of the at least one heavy olefin without the co-fed at least one light olefin.Type: GrantFiled: September 16, 1999Date of Patent: August 28, 2001Assignee: Phillips Petroleum CompanyInventor: Bruce B. Randolph
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Patent number: 6274783Abstract: A process is disclosed for the concurrent production and hydrogenation of diisobutene in a single distillation column reactor containing both a dimerization catalyst and a hydrogenation catalyst by the dimerized of isobutene to diisobutene. The catalysts may be in alternating beds or physically mixed together in one or more beds. Alternatively a bifunctional catalyst having both dimerization and hydrogenation properties may be used.Type: GrantFiled: March 20, 2000Date of Patent: August 14, 2001Assignee: Catalytic Distillation TechnologiesInventors: Gary R. Gildert, Mitchell E. Loescher
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Patent number: 6239321Abstract: A process for upgrading a feedstock comprising lower oligomers and higher oligomers of isobutylene by oligomerizing the lower oligomer fraction thereof to higher molecular weight components.Type: GrantFiled: February 28, 2000Date of Patent: May 29, 2001Assignee: BP Amoco CorporationInventors: Allen B. Mossman, Egils Vitands
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Patent number: 6222077Abstract: There is provided an alcohol composition obtained by dimerizing an olefin feed comprising C6-C10 linear olefins to obtain C12-C20 olefins, followed by conversion to alcohols, such as by hydroformylation. The composition has an average number of branches ranging from 0.9 to 2.0 per molecule. The linear olefin feed preferably comprises at least 85% of C6-C8-olefins. The primary alcohol compositions are then converted to anionic or nonionic surfactants, preferably sulfated or oxyalkylated or both. The sulfated compositions are biodegradable and possess good cold water detergency.Type: GrantFiled: April 2, 1998Date of Patent: April 24, 2001Assignee: Shell Oil CompanyInventor: David M. Singleton
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Patent number: 6143936Abstract: A process for producing an ether and an olefin from a hydrocarbon cut containing at least one tertiary olefin, comprises synthesis of at least one tertiary alkyl ether then fractionation to obtain an organic fraction (E1) which is enriched in the tertiary alkyl ether which is decomposed into a product containing at least one alcohol and at least one tertiary olefin, which is purified in a water washing extraction zone (L1) to obtain an aqueous fraction (A1) containing the major portion of the alcohol and a fraction (B1) containing the major portion of the tertiary olefin, at least a portion of fraction (B1) being sent to a separation zone (Co1) from which an aqueous liquid fraction (La1) and a liquid fraction (Lb1) containing the major portion of the tertiary olefin are recovered.Type: GrantFiled: April 1, 1998Date of Patent: November 7, 2000Assignee: Institut Francais du PetroleInventors: Marie-Claire Marion, Vincent Coupard, Alain Forestiere, Philippe Travers, Jean-Charles Viltard
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Patent number: 6133209Abstract: The present invention relates to at least simply unsaturated polyolefins with a number mean molecular weight in the range of 400 to 1,500 dalton and a dispersibility of M.sub.W /M.sub.N <1.2, obtained through catalytic dimerization from at least simply unsaturated olefin-oligomers, as well as to the method for their production. The present invention further relates to derivatives of these polyolefins which can be obtained by functionalizing at least a double link of the polyolefin. The invention also relates to the use of polyolefins and/or functionalization products as additives for fuels or lubricants.Type: GrantFiled: July 27, 1999Date of Patent: October 17, 2000Assignee: BASF AktiengesellschaftInventors: Hans Peter Rath, Irene Trotsch-Schaller, Dietmar Posselt, Bernhard Geissler, Johann-Peter Melder, Joachim Rosch
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Patent number: 6037514Abstract: Mixed electron- and proton-conducting metal oxide materials are provided. These materials are useful in fabrication of membranes for use in catalytic membrane reactions, particularly for promoting dehydrogenation of hydrocarbons, oligomerization of hydrocarbons and for the decomposition of hydrogen-containing gases. Membrane materials are perovskite compounds of the formula:AB.sub.1-x B'.sub.x O.sub.3-ywhere A=Ca, Sr, or Ba; B=Ce, Tb, Pr or Th; B'=Ti, V, Cr, Mn, Fe, Co, Ni or Cu; 0.2<x<0.5, and y is a number sufficient to neutralize the charge in the mixed metal oxide material.Type: GrantFiled: October 5, 1995Date of Patent: March 14, 2000Assignee: Eltron Research, Inc.Inventors: James H. White, Michael Schwartz, Anthony F. Sammells
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Patent number: 6031145Abstract: A catalyst composition for a process of oligomerising ethylene to produce 1-butene and/or 1-hexene wherein the catalytic composition is obtained by mixing at least one chromium compound with at least one aryloxy aluminum compound with general formula R.sub.n Al(R'O).sub.3-n where R is a linear or branched hydrocarbyl radical containing 1 to 30 carbon atoms, R'O is an aryloxy radical containing 6 to 80 carbon atoms and n is a whole number which can take the values 0, 1 or 2, and with at least one other hydrocarbyl aluminum compound selected from tris(hydrocarbyl)aluminum compounds or chlorinated or brominated hydrocarbyl aluminum compounds.Type: GrantFiled: June 17, 1998Date of Patent: February 29, 2000Assignee: Institut Francais du PetroleInventors: Dominique Commereuc, Sebastien Drochon, Lucien Saussine
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Patent number: 6013850Abstract: A process to maximize the production of low molecular weight alpha olefins from ethylene is disclosed. The process comprises oligomerizing ethylene in the presence of a catalyst, of titanium aryloxide and/or titanium alkoxide; alkyl aluminum halide and triaryl phosphine and/or trialkyl phosphine in the temperature range of 80.degree. C. to 110.degree. C. at substantially low pressures of from 60 to 150 psi. A continuous supply of ethylene is maintained.Type: GrantFiled: April 8, 1997Date of Patent: January 11, 2000Assignee: Indian Petrochemicals Corporation LimitedInventors: G. L. Tembe, S. Muthukumaru Pillai, Sheo Satish, M. Ravindranathan
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Patent number: 6011191Abstract: A process is described for the production of hydrocarbons with a high octane number starting from hydrocarbon cuts containing isobutene by selective dimerization with acid catalysts characterized in that the dimerization reaction is carried out in the presence of primary alcohols and alkyl others in such a quantity as to have in the feeding a molar ratio primary alcohols+alkyl ethers/isobutene of more than 0.1 and a molar ratio primary alcohols/isobutene of less than 0.2, operating, preferably, at a reaction temperature of between 30 and 120.degree. C., at a pressure of less than 5 MPa and feeding space velocities of less than 30 h.sup.-1.Type: GrantFiled: May 15, 1998Date of Patent: January 4, 2000Assignee: Snamprogetti S.p.A.Inventors: Marco Di Girolamo, Lorenzo Tagliabue
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Patent number: 6008426Abstract: The conversion of n-olefins, particularly n-butene, by skeletal isomerization, or by dimerization optionally with cracking, may be selectively carried out using as a catalyst a molecular sieve, such as a zeolite or silica/alumina phosphate, which has been ion exchanged with a cation to provide a Lewis acid site. No steam activation of the molecular sieve is required.Type: GrantFiled: June 2, 1998Date of Patent: December 28, 1999Assignee: Exxon Chemical Patents Inc.Inventors: Cornelius W. M. Van Oorschot, Michiel Makkee, Marcel J. G. Janssen, Wilfried J. Mortier
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Patent number: 6002061Abstract: A monoolefin oligomerization process which gives high yields of diner and trimer at high monoolefin conversions in a single stage reaction is described. The process involves contacting a C.sub.6-20 oligomerizable olefin with a catalyst comprising boron trifluoride and from 0.05 to 2.5 mol %, based on the total quantity of monoolefin being used, of an alcohol catalyst promoter which is added portionwise during the oligomerization. The oligomerization is performed at a temperature of 45-90.degree. C. and under a pressurized atmosphere of boron trifluoride until the monoolefin conversion is at least 90% and the combined total of dimer and trimer in the liquid reaction mixture is at least 70% by weight.Type: GrantFiled: September 11, 1996Date of Patent: December 14, 1999Assignee: BP Amoco CorporationInventor: Michel Clarembeau
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Patent number: 5994601Abstract: A process is described in which butene oligomers are prepared from Fischer-Tropsch olefins, in which the butenes present in a C.sub.4 fraction of Fischer-Tropsch hydrocarbons are oligomerized to obtain dibutene. The dibutene can be fractionated in a fine distillation stage into di-n-butene and di-isobutene. In one embodiment of the process, the ethylene present in the Fischer-Tropsch olefins is dimerized and the dimerization mixture is recycled to the C.sub.4 fraction. In another embodiment, the isobutene present in the C.sub.4 fraction is reacted with an alcohol to give an alkyl tert-butyl ether, and only the remaining n-butene is oligomerized so that di-n-butene is formed as the sole dibutene.Type: GrantFiled: July 24, 1997Date of Patent: November 30, 1999Assignee: Huels AktiengesellschaftInventors: Franz Nierlich, Walter Toetsch, Paul Olbrich, Wilhelm Droste, Richard Mueller
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Patent number: 5973219Abstract: A process for controlling the molecular weight distribution of polyisobutene formed during a liquid phase polymersiation reaction using a catalyst comprising boron trifluoride and taking place in a reactor having condensers associated with it which process involves introducing an electron donor above the level of liquid in the reactor to minimize the reaction of isobutene with free gaseous boron trifluoride in the condensers thereby minimizing the formation of unwanted polymers.Type: GrantFiled: March 26, 1998Date of Patent: October 26, 1999Assignee: BP Chemicals LimitedInventors: Derek Alan Colman, James Maxwell Kerr
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Patent number: 5962604Abstract: Low molecular weight, highly reactive polyisobutene having an average molecular weight M.sub.n of from 500 to 20000 Dalton and containing over 80 mol % of terminal double bonds is prepared by the polymerization of isobutene or an isobutene-containing hydrocarbon stream in the liquid phase and with the aid of a boron trifluoride complex catalyst at from -40 to 0.degree. C. and at from 1 to 20 bar, by a process in which the polymerization reaction is carried out in at least two polymerization stages, the added isobutene being polymerized to a partial conversion of up to 95% in the first polymerization stage and the polymerization of the remaining isobutene being continued in one or more subsequent polymerization stages, without or after prior isolation of the polyisobutene formed in the first polymerization stage.Type: GrantFiled: November 25, 1997Date of Patent: October 5, 1999Assignee: BASF AktiengesellschaftInventor: Hans Peter Rath
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Patent number: 5945574Abstract: The use of novel heterogeneous catalyst complexes as catalysts for oligomerizing alpha-olefins is disclosed. The complexes are formed from (i) a solid olefin polymer having a linear backbone and a plurality of pendant omega-hydroxyalkyl groups, (ii) an organomagnesium halide, and (iii) a boron trihalide, preferably BF.sub.3. The complexes can be recovered and reused repeatedly in batch-type operations and can be used for long periods of time in continuous or semi-continuous operations without replenishment of their boron trifluoride content.Type: GrantFiled: December 13, 1995Date of Patent: August 31, 1999Assignee: BP Amoco CorporationInventors: Tze-Chiang Chung, Ruidong Ding, Ronald L. Shubkin
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Patent number: 5929297Abstract: Alpha-olefin oligomers are produced by oligomering alpha-olefin monomer with a catalyst system comprising boron trifluoride, a protic promoter, and a special type of modifier. The modifier is a compound that satisfies the following criteria: (a) it has at least one moiety in which a carbonyl group is directly bonded to a nitrogen atom which is in turn bonded to two separate carbon atoms, (b) it is devoid of any nitrogen atom other than a nitrogen atom that is either (i) directly bonded to two separate carbon atoms and to a carbonyl group or (ii) is triply bonded to a single carbon atom, and (c) it is devoid of any protonic functional substituent. These modifiers control the oligomer product distribution and provide higher percentages of lower oligomers, especially dimers.Type: GrantFiled: September 25, 1997Date of Patent: July 27, 1999Assignee: BP Amoco CorporationInventors: Kevin J. Theriot, Robert G. Irwin
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Patent number: 5919996Abstract: A process is provided to modify an olefin production catalyst system which comprises contacting an olefin production catalyst system with ethylene prior to use. A process also is provided to trimerize and/or oligomerize olefins with the novel, modified olefin catalyst production system. The modified olefin production catalyst system produces less solids, such as, for example, polymer.Type: GrantFiled: October 13, 1998Date of Patent: July 6, 1999Assignee: Phillips Petroleum CompanyInventors: Jeffrey W. Freeman, John L. Buster, Ronald D. Knudsen
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Patent number: 5910550Abstract: Polyisobutene having an average molecular weight M.sub.n of from above 5000 to 80,000 dalton and containing more than 50 mol % of terminal double bonds is prepared by a novel process, by cationic polymerization of an isobutene-containing hydrocarbon mixture in. the liquid phase in the presence of a boron trifluoride complex catalyst, and has a dispersity of M.sub.w /M.sub.n of from 2 to 4 and is contained in lubricants.Type: GrantFiled: May 6, 1997Date of Patent: June 8, 1999Assignee: BASF AktiengesellschaftInventor: Hans Peter Rath
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Patent number: 5910618Abstract: 2,3-Dimethyl-2-butene is prepared by isomerizing 2,3-dimethyl-1-butene using at least one acid selected from the group consisting of sulfuric acid and sulfonic acids. By this process, 2,3-dimethyl-2-butene is effectively prepared from 2,3-dimethyl-1-butene using an inexpensive catalyst such as sulfonic acid or the sulfonic acids. Further, a dimerization reaction product of propene can also be used in the isomerization step without removing the dimerization catalyst from the reaction product.Type: GrantFiled: March 19, 1997Date of Patent: June 8, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Kotohiro Nomura, Michio Yamamoto, Masashi Komatsu
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Patent number: 5877375Abstract: A monoolefin oligomerization process which gives high yields of dimer and trimer at high monoolefin conversions in a single stage reaction is described. The process involves contacting a C.sub.6-20 vinyl olefin with a catalyst comprising boron trifluoride and from 0.075 to 0.5 mol %, based on the total quantity of monoolefin being used, of an alcohol catalyst promoter. The oligomerization is performed at a temperature below about 40.degree. C. and under a pressurized atmosphere of boron trifluoride in the range of 2 to 4 bars gauge until the monoolefin conversion is at least 95% and the combined total of dimer and trimer in the liquid reaction mixture is at least 60% by weight.Type: GrantFiled: June 6, 1996Date of Patent: March 2, 1999Assignee: Amoco CorporationInventor: Michel Clarembeau
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Patent number: 5877372Abstract: A process is provided for the production of a gasoline blending fraction rich in isooctane by the dimerization of isobutylene using tertiary butyl alcohol modifier and isoalkane diluent; advantageously the isobutylene is derived from the dehydration of tertiary butyl alcohol and the isoalkane used as diluent in the dimerization is the product formed by hydrogenation of the oligomerization product.Type: GrantFiled: November 21, 1997Date of Patent: March 2, 1999Assignee: Arco Chemical Technology, L.P.Inventors: Thomas I. Evans, Lawrence J. Karas, Ramesh Rameswaran
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Patent number: 5859159Abstract: An improved process for the homopolymerization and copolymerization of .alpha.-olefins utilizing highly dilute .alpha.-olefin feedstreams to effect high conversions and catalyst efficiencies in the production of non-ethylene copolymers. The instant invention is particularly adaptable to polymerizing the .alpha.-olefin content of commercially available refinery feedstreams such as Raffinate-2.Type: GrantFiled: March 14, 1997Date of Patent: January 12, 1999Assignee: Exxon Chemical Patents Inc.Inventors: Albert Rossi, Salvatore Rea, Jon E. Stanat, Linda K. Wright, Kenneth L. Kaufman, Jeffrey W. Frederick, Robert Martin Koros, Harold Wilbur Margo
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Patent number: 5859303Abstract: A process is provided to trimerize or oligomerize olefins in the presence of an olefin oligomerization catalyst and a solvent which is a product of the olefin oligomerization process.Type: GrantFiled: December 18, 1995Date of Patent: January 12, 1999Assignee: Phillips Petroleum CompanyInventor: Mark E. Lashier
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Patent number: 5817899Abstract: A dimer composition has an improved low temperature viscosity if it has less than a certain amount of normal paraffin. A 1-octene dimer should have less than 0.50 wt. % normal hexadecane, a 1-decene dimer should have less than 0.05 wt. % normal eicosane, a 1-dodecene dimer should have less than 0.60 wt. % normal tetracosane, and a 1-tetradecene dimer should have less than 0.10 wt. % normal octacosane.Type: GrantFiled: June 16, 1997Date of Patent: October 6, 1998Assignee: Chevron Chemical CompanyInventors: Kenneth D. Hope, Ting C. Ho, Barrett L. Cupples
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Patent number: 5817902Abstract: The invention provides a process for making .alpha.-olefins. In the chain growth reaction step of the process a jet loop reactor is used to fully use high pressure ethylene, and two or more stages of the chain growth reaction is used to raise the selectivity of C.sub.6-10 olefins.Type: GrantFiled: November 12, 1996Date of Patent: October 6, 1998Assignees: China Petro-Chemical Corporation, Daqing Petrochemical Works, China Petrochemical CorporationInventors: Minghe Xie, Anshun Sun, Daohua Jiang, Jiabo Qu, Qian Chen, Weibin Li, Zongsheng Yuan, Chunmei Yu, Xixia Song, Shubao Wan, Zhengnian Luo, Fengrong Wang, Qun Xu, Shulan Wang, Yingjie Feng, Yongchen Sun
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Patent number: 5811617Abstract: Alpha-olefin oligomer is prepared by contacting an alpha-olefin monomer which contains from about 8 to about 16 carbon atoms with a heterogeneous catalyst system formed from (i) a solid olefin polymer having a linear backbone and a plurality of pendant omega-hydroxyalkyl groups, and (ii) a boron trihalide, preferably BF.sub.3. The catalyst system is stable and very reactive at relatively high temperatures, and the solid polymer of the catalyst system can be recovered and reused repeatedly in batch-type operations and can be used for long periods of time in continuous or semi-continuous operations.Type: GrantFiled: December 13, 1995Date of Patent: September 22, 1998Assignee: Amoco CorporationInventors: Ronald L. Shubkin, Tze-Chiang Chung, Ruidong Ding
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Patent number: 5792895Abstract: The invention concerns an improved process for the conversion of ethylene into but-1-ene, wherein the ethylene is brought into contact with a catalyst obtained by the interaction of an alkyl titanate, possibly mixed with an ether, with a compound of aluminium of the formula AlR.sub.3 or AlR.sub.2 H, and in the presence of an additive formed by at least one polyethylene glycol and/or one of its derivatives such as a monoether or a monoester of polyethylene glycol.Type: GrantFiled: April 24, 1997Date of Patent: August 11, 1998Assignees: Institut Francais du Petrole, Saudi Basic Industries CorporationInventors: Dominique Commereuc, Yves Chauvin, Francois Hugues, Yves Glaize
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Patent number: 5780688Abstract: The invention concerns a supported catalyst in the form of packing and constructed on an open-pore support material on whose external and internal surfaces a macro-porous ion exchange resin is mechanically and/or chemically affixed.Type: GrantFiled: April 5, 1996Date of Patent: July 14, 1998Assignee: Veba Oel AGInventors: Ulrich Hoffmann, Ulrich Kunz, Hartmut Bruderreck, Klaus Gottlieb, Kuno Schadlich, Stefan Becker
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Patent number: 5750821Abstract: The following steps are conducted for producing a hydrocarbon having a carbon number of at least 2: a coupling step, in which a coupling feed gas containing methane and a gas containing oxygen are supplied to a conveying catalyst bed which is formed by an ascending stream which contains a catalyst, and then methane and oxygen are allowed to react so as to produce a coupling product gas; a catalyst separation step for separating the catalyst from the coupling product gas; and a catalyst feedback step for feeding back the thus-separated catalyst to the coupling step. Accordingly, the reaction system does not accumulate excessive heat, the combustion reaction as a side reaction is hindered, and the selectivity of the coupling reaction is enhanced. In addition, the yield of the hydrocarbon having a carbon number of at least 2 is improved.Type: GrantFiled: November 21, 1995Date of Patent: May 12, 1998Assignees: Japan National Oil Corporation, Sekiyushigen Kaihatsu Kabushiki Kaisha, Cosmo Research InstitueInventors: Makoto Inomata, Tsutomu Katagiri, Kozo Imura, Erli Sun
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Patent number: 5744676Abstract: Alpha-olefin oligomers are produced by oligomerizing an alpha-olefin monomer with a catalyst system comprising boron trifluoride, a protic promoter, and a modifier which is (a) at least one 1,3-dioxolane, or (b) at least one 1,3-dioxane, or (c) a combination of (a) and (b). Use of these modifiers in the BF.sub.3 -catalyzed oligomerization makes it possible to modify the promoted catalytic reaction so that product containing as much as 50% or more of dimer can be produced at high conversions, at modest reaction temperatures, and in short reaction periods.Type: GrantFiled: February 26, 1996Date of Patent: April 28, 1998Inventors: Kevin J. Theriot, Robert G. Irwin
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Patent number: 5731486Abstract: A method for producing 3-methyl-2-pentene which is substantially free of any other C.sub.6 olefin, except 2-ethyl-1-butene, by first producing a stream that contains 2-ethyl-1-butene from the trimerization of ethylene, and second by recovering the 2-ethyl-1-butene as 3-methyl-2-pentene via etherification, separation of the ether, and decomposition of the ether back to predominantly 3-methyl-2-pentene with some 2-ethyl-1-butene.Type: GrantFiled: July 17, 1995Date of Patent: March 24, 1998Assignee: Exxon Chemical Patents IncInventors: Dan E. Hendriksen, Gerald G. McGlamery, Michael J. Keenan, Derrick D. Pete
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Patent number: 5731487Abstract: The present invention provides a process for producing olefin having a terminal double bond by trimerizing at least one monomer selected from a group consisting of ethylene, propylene, and 1-butene, which comprises using a catalyst comprising a product prepared from(1) component (A): a chromium compound represented by the formula ?1!CrXmYn ?1!wherein X represents carboxylic acid residue, 1,3-diketone residue, halogen atom or alkoxyl group, Y represents amine, phosphine, phosphine oxide, nitrosyl group or ether, m means an integer of from 2 to 4 and n means an integer of from 0 to 4,component (B): a heterocyclic compound having a pyrrole ring unit or an imidazole ring unit, andcomponent (C): an aluminum compound represented by the formula ?2!AlR.sub.k Z.sub.Type: GrantFiled: August 9, 1996Date of Patent: March 24, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Mitsuhisa Tamura, Kenshi Uchida, Yoshiaki Ito, Kiyoshi Iwanaga
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Patent number: 5728912Abstract: The process of butene-1 production comprises the steps of: a) sending a inhibited catalyst containing reactor effluent to a flash section where the pressure is decreased by about 0.1 MPa to about 2 MPa, and obtaining a first gaseous phase containing ethylene and butene-1 and a first liquid phase containing the inhibited catalyst; b) sending the first liquid phase from step a) to at least one vaporisation section which allows the separation of a second gaseous phase containing butene-1 and ethylene from a second liquid phase containing the inhibited catalyst; c) sending the second liquid phase from step b) to at least one thin film evaporation section which allows the separation of a third gaseous phase containing ethylene, butene-1 and some other heavier hydrocarbon products from a concentrated inactivated catalyst solution and, d) collecting the first, second and third gaseous phases to form a gaseous reactor effluent substantially free of spent catalyst.Type: GrantFiled: April 29, 1996Date of Patent: March 17, 1998Assignees: Institut Francais du Petrole, Saudi Basic Industries Corp.Inventors: Syed Saqualain Haider Rizvi, Fahad Abdulaziz Al Sherehy, Moayyed Issa Al-Qurtas, Alain Forestiere, Jean Gaillard
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Patent number: 5723713Abstract: This invention relates to a process for the converting ethylene to a mixture of 1-olefins by (a) feeding ethylene through an oligomerization catalyst bed to form an oligomer predominating in C2-C6 olefins and (b) feeding the oligomer, optionally admixed with fresh ethylene, containing at least 50% by volume ethylene, through a metathesis catalyst bed to form a product predominating in C2-C6 1-olefins. Steps (a) and (b) can be carried out sequentially and in a single reactor under the same conditions of reaction temperature and pressure. This mitigates the perceived disadvantages of low activity and low conversions of relatively inexpensive oligomerization catalysts and forms oligomer having the desired distribution of 1-olefin components for use as comonomer in a polyolefin process.Type: GrantFiled: August 6, 1996Date of Patent: March 3, 1998Assignee: BP International LimitedInventor: Barry Martin Maunders
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Patent number: 5710225Abstract: Phosphotungstic acid salts are used to polymerize C.sub.2 -C.sub.30 .alpha.-olefins and derivatives thereof to form highly reactive products having a high content of terminal vinylidene groups and .beta.-isomers in resonance therewith. Isobutylene has been polymerized to form a Mn 300-20,000 polymer.Type: GrantFiled: August 23, 1996Date of Patent: January 20, 1998Assignee: The Lubrizol CorporationInventors: John R. Johnson, James D. Burrington
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Patent number: 5650548Abstract: Alpha-olefin oligomer is prepared by contacting an alpha-olefin monomer which contains from about 6 to about 20 carbon atoms with a catalyst system comprising boron trifluoride, a protic promoter, and an organic sulfone, sulfoxide, carbonate, thiocarbonate, or sulfonate. Oligomer containing as much as 50% or more of dimer can be produced at high conversions, at modest reaction temperatures, and in acceptably short reaction periods.Type: GrantFiled: June 16, 1995Date of Patent: July 22, 1997Assignee: Amoco CorporationInventors: Kevin J. Theriot, Robert G. Irwin
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Patent number: 5633420Abstract: Alpha-olefin oligomers are prepared by a process which comprises contacting an oligomerizable olefin monomer with a catalyst system comprising a catalytic amount of boron trifluoride, a protic promoter, and an organic modifier selected from the group consisting of phosphate, thiophosphate, phosphine oxide, and phosphine sulfide. The oligomerizable olefin monomer is a C.sub.6 to C.sub.20 linear olefin comprising at least 50 mole % alpha olefin.Type: GrantFiled: September 22, 1995Date of Patent: May 27, 1997Assignee: Amoco CorporationInventors: Kevin J. Theriot, Robert G. Irwin
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Patent number: 5625106Abstract: A new class of olefin dimerization catalysts and an efficient method for their preparation is disclosed. B (C.sub.6 F.sub.5).sub.3 reacts quantitatively with Group 4 metallocene type catalysts to yield highly reactive cationic complexes as follows:(L.sub.2 MR.sup.2).sup.+ X.sup.- whereL=R.sub.2 (C.sub.5 H.sub.3); R=CR'.sub.3 ; R.sup.2 =alkyl group (C=1.ltoreq.20);M=Ti, Zr, Hf;X.sup.- =RB(C.sub.6 F.sub.5).sub.3.sup.-, or methylalumoxane.These complexes are potent catalysts and may be used in the dimerization of .alpha.-olefins.Type: GrantFiled: December 11, 1995Date of Patent: April 29, 1997Assignee: Northwestern UniversityInventors: Tobin J. Marks, Xinmin Yang
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Patent number: 5589601Abstract: The invention concerns a process for dimerization, co-dimerization and oligomerization of olefins, in particular .alpha.-olefins, with a catalytic composition resulting from a mixing at least one tungsten oxyhalide, at least one aryl isocyanate of diisocyanate, and at least one alkylaluminum halide.Type: GrantFiled: September 15, 1995Date of Patent: December 31, 1996Assignee: Institut Francais du PetroleInventors: Yves Chauvin, H el ene Olivier
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Patent number: 5563312Abstract: A process is provided to stabilize and/or reactivate an olefin production catalyst system which comprises contacting an olefin production catalyst system, either before or after use, with an aromatic compound.Type: GrantFiled: May 19, 1995Date of Patent: October 8, 1996Assignee: Phillips Petroleum CompanyInventors: Ronald D. Knudsen, Jeffrey W. Freeman, Mark E. Lashier
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Patent number: 5557023Abstract: The present invention relates to the oligomerization of lower alpha olefins, and particularly ethylene, to higher olefins in the presence of a catalyst precursor having either or both of a dithiophosphinate complex and a heterobifunctional ligand having a phosphine center and an imine or similar center, in the presence of an activator. The catalysts have a high reactivity and a good selectivity.Type: GrantFiled: May 23, 1995Date of Patent: September 17, 1996Assignee: The Governors of the University of AlbertaInventors: Arpad F. Somogyvari, Beth L. Creed, Antonio P. Nicola, Alan R. Sanger, David J. Law, Ronald G. Cavell
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Patent number: 5550307Abstract: An oligomer is made by contacting an olefinic monomer with a catalyst comprising boron trifluoride, an alcohol alkoxylate, and a ketone. In one embodiment, the olefinic monomer is a straight-chain, .alpha.-olefinic monomer containing from 8 to 12 carbon atoms, the alcohol alkoxylate is 2-ethoxyethanol, the ketone is methyl ethyl ketone, and the oligomer product has a kinematic viscosity at 100.degree. C. of less than 1.7 cSt. Before removal of unreacted monomer, the oligomer product is at least 50 wt. % dimer, at least 80 wt. % dimer plus trimer, and less than 3.25 wt. % tetramer and greater.Type: GrantFiled: August 31, 1994Date of Patent: August 27, 1996Assignee: Chevron Chemical CompanyInventors: Kenneth D. Hope, Ting C. Ho, Barrett L. Cupples
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Patent number: 5550306Abstract: The invention is concerned with a process for the dimerization, co-dimerization and oligomerization of olefins with a catalytic composition resulting from mixing at least one quaternary ammonium halide and/or at least one quaternary phosphonium halide, at least one aluminum halide, at least one aromatic hydrocarbon and optionally an aluminium organometallic compound.Type: GrantFiled: June 1, 1995Date of Patent: August 27, 1996Assignee: Institut Francais du PetroleInventors: Yves Chauvin, Sandra Einloft, Helene Olivier
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Patent number: 5550304Abstract: The invention concerns a catalytic composition and a process for the dimerisation, codimerisation or oligomerisation of olefins, said composition comprising a mixture of at least one bivalent nickel complex which contains two tertiary phosphine molecules, at least one nickel complex which contains neither water nor phosphine, and at least one alkylaluminium halide. The mixture is particularly for use in ionic type non aqueous liquid compositions, such as those formed by quaternary ammonium halides and/or quaternary phosphonium halides with aluminium halides and/or alkylaluminium halides.Type: GrantFiled: May 26, 1995Date of Patent: August 27, 1996Assignee: Institut Francais Du PetroleInventors: Yves Chauvin, Sandra Einloft, Helene Olivier
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Patent number: 5545789Abstract: The invention relates to a process for the dimerization of a conjugated diene using an iron triad metal nitrosyl halide, in combination with a reducing agent, as catalyst. The process is characterized in that the dimerization is carried out in the presence of nitrogen monoxide (NO). The invention is of interest in particular for the dimerization of butadiene to 4-vinyl cyclohexene.Type: GrantFiled: May 5, 1995Date of Patent: August 13, 1996Assignee: DSM N.V.Inventors: Henricus A. M. Duisters, Johan G.D. Haenen
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Patent number: 5545790Abstract: A catalytic process for the dimerization of norbornene and/or norbornadiene using a reduced valence state Group VIB metal oxide as the catalyst, preferably Cr(II) on a porous support such as silica. The product norbornene dimer or norbornadiene dimer is obtained in high yield and high stereospecificity at greater than 90 weight percent of the exo-trans-exo stereoisomer. The norbornene dimer is useful as a high energy density fuel. The norbornadiene dimer can be further functionalized to yield novel chemical intermediates or polymerized or copolymerized with other olefins. The norbornadiene dimer can also be hydrogenated for high energy fuel applications.Type: GrantFiled: December 9, 1993Date of Patent: August 13, 1996Assignee: Mobil Oil CorporationInventors: Margaret M. Wu, Yusheng Xiong
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Patent number: 5510555Abstract: A catalyst, which is active in the oligomerization of olefins is an X-ray-amorphous silica-alumina-nickel oxide gel having an SiO.sub.2 /Al.sub.2 O.sub.3 molar ratio of from 30/1 to 500/1, and NiO/SiO.sub.2 molar ratio of from 0.001/1 to 0.01/1, a superficial area of from 500 m.sup.2 /g to 1.000 m.sup.2 /g, and a porosity of from 0.3 ml/g to 0.6 ml/g, the means pore diameter being 1 nm (10 Angstrom), and devoid of pores having a diameter over 3 nm (30 Angstrom). The catalyst selectively dimerizes isobutene into alpha- and beta-isobutene and oligomerizes propylene into its relative dimers and trimers. A process is described for preparing the silica-alumina-nickel oxide gel.Type: GrantFiled: February 10, 1994Date of Patent: April 23, 1996Assignee: Eniricerche, S.p.A.Inventors: Maurizio Brunelli, Walter Castelvetro, Giuseppe Bellussi, Stefano Peratello
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Patent number: 5502264Abstract: 1-pentene dimers of .alpha.-methylstyrenes are produced with high selectivity in good productivity by stirring 50 to 95 parts by weight of an .alpha.-methylstyrene in the presence of 50 to 5 parts by weight of an aqueous solution of a sulfonic acid, and a 1-pentene dimer having good preservative property is then collected by removing the sulfonic acid, adjusting the resulting reaction solution to pH 8 or higher and distilling the neutralized reaction solution.Type: GrantFiled: May 18, 1994Date of Patent: March 26, 1996Assignee: Goi Chemical Company, Ltd.Inventors: Hiroshi Nishizawa, Takayuki Saitoh, Tatsuo Itoh, Kiyotaka Mashita