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: 5475162Abstract: A process of effecting an acid catalyzed reaction wherein a reactant capable of undergoing an acid catalyzed reaction is contacted with an acid functionalized organically-bridged polysilsesquioxane catalyst where all of the acid functionality is covalently bonded to the organic portion of an organically-bridged polysilsesquioxane framework has been developed. The acid functionalized organically-bridged polysilsesquioxane is formed by polymerizing a monomer through sol-gel processing to form an organically-bridged polysilsesquioxane, reacting an acid group onto the organic portion of the organically-bridged polysilsesquioxane, and recovering the acid functionalized product. An embodiment of the invention is where the acid catalyzed reaction is the hydration of olefins, alkylation, acylation, isomerization, or aldol condensation/elimination.Type: GrantFiled: July 19, 1994Date of Patent: December 12, 1995Assignee: UOPInventors: Timothy A. Brandvold, Jennifer S. Holmgren, Thomas P. Malloy
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Patent number: 5475178Abstract: There is provided a catalyst comprising a heteropoly acid, such as phosphotungstic acid, supported on a mesoporous crystalline material, such as M41S. A particular form of this M41S support is designated as MCM-41. There is also provided a method for preparing this catalyst by impregnating the heteropoly acid on the support. There is also provided a process for using this catalyst to catalyze acid catalyzed reactions, such as the isomerization of paraffins and the alkylation of aromatics.Type: GrantFiled: August 18, 1994Date of Patent: December 12, 1995Assignee: Mobil Oil Corp.Inventors: Kenneth J. Del Rossi, Gregory A. Jablonski, Charles T. Kresge, Guenter H. Kuehl, David O. Marler, Gayatri S. Rav, Brenda H. Rose
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Patent number: 5457254Abstract: 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 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 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: December 27, 1993Date of Patent: October 10, 1995Assignee: 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: 5401896Abstract: Relatively long chain alkyl aromatic compounds are prepared by alkylating an alkylatable aromatic compound with a relatively long chain alkylating agent under alkylation reaction conditions in the presence of catalyst comprising zeolite MCM-49.Type: GrantFiled: November 23, 1992Date of Patent: March 28, 1995Assignee: Mobil Oil Corp.Inventors: Guenter H. Kuehl, Daria N. Lissy, Hye Kyung C. Timken
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Patent number: 5396011Abstract: An aromatic compound (such as benzene) is alkylated with a alkene (such as propylene) by contacting the two compounds together in the presence of a tungsten on zirconia catalyst. The reaction preferably takes place at elevated temperature and elevated pressure. The process of the invention has very high selectivity and conversion, and produces no or only very low amounts of undesirable oligomers (as measured by bromine number).Type: GrantFiled: December 28, 1992Date of Patent: March 7, 1995Assignee: Mallinckrodt Chemical, Inc.Inventor: Deborah K. Kuhn
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Patent number: 5386072Abstract: Process for the preparation of linear alkylbenzenes, wherein the benzene is reacted, in the presence of aluminum chloride or aluminum in powder form, with a mixture composed of C.sub.7 -C.sub.20 n-olefins and C.sub.7 -C.sub.20 chloroparaffins, with a molar ratio n-olefins/chloroparaffins between 70:30 and 99:1.Type: GrantFiled: January 29, 1993Date of Patent: January 31, 1995Assignee: Enichem Augusta S.p.A.Inventors: Pierluigi Cozzi, Giuseppe Giuffrida, Tullio Pellizzon, Pierino Radici
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Patent number: 5347062Abstract: An alkyl-substituted hydrocarbon is prepared by alkylating an aromatic hydrocarbon having at least one hydrogen atom at an alpha-position in a side chain with an olefin in the presence of a solid base which is obtainable by heating an alumina, an alkali metal hydroxide and an alkali metal or an alumina containing at least 1.3% by weight of water and an alkali metal in an inert gas atmosphere at a specific temperature as a catalyst.Type: GrantFiled: February 24, 1993Date of Patent: September 13, 1994Assignee: Sumitomo Chemical Co., Ltd.Inventors: Masami Fukao, Takuo Hibi, Kazuo Kimura, Masahiro Usui, Gohfu Suzukamo
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Patent number: 5344997Abstract: A fluorided silica-alumina catalyst, particularly one with a silica:alumina ratio in the range of 1:1-9:1 containing from 1 to 6 weight percent fluoride, is particularly effective in the liquid phase alkylation of benzene by linear olefins to produce linear alkyl benzenes at temperatures no greater than 140.degree. C. These catalysts also are effective in the liquid phase alkylation of alkylatable aromatics generally with a variety of alkylating agents, including olefins, alcohols, and alkyl halides.Type: GrantFiled: December 14, 1992Date of Patent: September 6, 1994Assignee: UOPInventor: Joseph A. Kocal
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Patent number: 5342532Abstract: A lubricating oil composition comprises an alkylnaphthalene which has one or two alkyl groups each having from 8 to 30 carbon atoms, and at least one member selected from benzo(b)thiophene and derivatives thereof, and naphthalenethiol and derivatives thereof. The composition has good oxidative stability.Type: GrantFiled: September 23, 1992Date of Patent: August 30, 1994Assignee: Nippon Oil Company, Ltd.Inventors: Mitsuhiko Takei, Toshio Yoshida, Yoshiaki Nagai, Koji Masamizu
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Patent number: 5302769Abstract: A polycyclic aromatic is contacted with an alkyl-substituted single ring aromatic, such as toluene, o-, m- or p-xylene or mesitylene, over a catalyst comprising a zeolite, such as zeolite beta, USY or ZSM-5 to alkylate the polycyclic aromatic. The polycyclic aromatic can be a fused polynuclear aromatic, e.g. phenanthrene, or an assembly of two or more cyclic systems, e.g. biphenyl. The polycyclic aromatic can also include carbocyclic systems such as fluorene and naphthalene or heterocyclic systems such as benzothiophene and dibenzothiophene. The polycyclic aromatic can be derived from a cycle oil, coker gas oil, extract of lubricant solvent refining or crude distillate fraction. The transalkylating agent can be derived from a reformate, pyrolysis gasoline or coker naphtha.Type: GrantFiled: December 7, 1992Date of Patent: April 12, 1994Assignee: Mobil Oil CorporationInventors: David O. Marler, Dominick N. Mazzone, L. Deane Rollmann
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Patent number: 5302732Abstract: Silica-aluminas having a sodium content less than about 0.1 weight percent show increased stability when used as a catalyst for the alkylation of aromatic compounds. Where such silica-aluminas are used as the catalyst in detergent alkylation their increased stability permits continuous alkylation to be performed at lower temperatures, as a result of which the detergent alkylate product shows an incrementally higher linearity. Fluorided silica-aluminas having a sodium content of under 0.05 weight percent are particularly advantageous.Type: GrantFiled: September 14, 1992Date of Patent: April 12, 1994Assignee: UOPInventors: Karl Z. Steigleder, Christine M. Conway, David M. Baldwin, Diane C. Dierking
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Patent number: 5268524Abstract: Essentially linear alkyl aromatics wherein the alkyl is attached to the aromatic ring at the .beta.-position are produced by the process wherein a linear hydrocarbon selected from the group consisting of linear .alpha.-olefins, linear .alpha.-substituted alkyl halides or linear .alpha.-substituted alkyl alcohol or mixtures of such olefins, halides or alcohols are reacted with an aromatic compound in the presence of an aprotic-polar cosolvent.Type: GrantFiled: September 24, 1992Date of Patent: December 7, 1993Assignee: Exxon Chemical Patents Inc.Inventors: David J. Martella, John J. Jaruzelski, Frank J. Chen
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Patent number: 5196574Abstract: A fluorided silca-alumina catalyst, particularly one with a silica:alumina ratio in the range of 1:1-9:1 containing from 1 to 6 weight percent fluoride, is particularly effective in the liquid phase alkylation of benzene to produce linear alkyl benzenes at temperatures no greater than 140.degree. C. Conversions in excess of 98% with selectivity exceeding 85% and linearity exceeding 90% may be achieved readily.Type: GrantFiled: December 23, 1991Date of Patent: March 23, 1993Assignee: UOPInventor: Joseph A. Kocal
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Patent number: 5191135Abstract: Long chain alkyl substituted aromatic compounds, particularly alkylated naphthalenes, are produced by the alkylation of aromatics, e.g. naphthalene, with an olefin or other alkylating agent possessing at least 6 carbon atoms, usually 12 to 20 carbon atoms, in the presence of a zeolite alkylation catalyst, preferably a large pore size zeolite such as zeolite Y and in the presence of from about 0.5 to 3.0 weight percent water, preferably 1.0 to 3.0 weight percent. The use of the water co-feed increases the selectivity of the alkylation for the production of long chain mono-alkyl substituted naphthalenes in preference to more highly substituted products and also increases activity and catalyst stability.Type: GrantFiled: March 25, 1991Date of Patent: March 2, 1993Assignee: Mobil Oil CorporationInventors: Francis G. Dwyer, Quang N. Le
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Patent number: 5177284Abstract: This application discloses critical parameters, including process conditions and catalysts which effect the alpha:beta ratio of alkylated naphthalene isomers. The use of low alkylation temperatures and of low acidity zeolite catalysts (e.g. steamed USY and zeolite beta) lead to an increase in the alpha:beta ratio. The alkylated naphthalene fluids with higher alpha:beta ratio exhibited significantly enhanced product qualities, including thermal and oxidative stabilities.Type: GrantFiled: May 28, 1991Date of Patent: January 5, 1993Assignee: Mobil Oil CorporationInventors: Quang N. Le, Joosup Shim
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Patent number: 5171915Abstract: It is disclosed that aromatic compounds can be alkylated with mono-olefinic HVI-PAO dimer in contact with an acidic catalyst to produce novel alkylated aromatic compositions. It has been found that the novel HVI-PAO dimer alkylated aromatic compositions exhibit an extraordinary combination of properties relating to low viscosity with high viscosity index and low pour point which renders them very useful as lubricant basestock. Further, it has been found that the novel alkylaromatic compositions of the present invention show improved oxidative stability. Depending upon the substituent groups on the aromatic nucleus, useful lubricant additives can be prepared for improved antiwear, antioxidant and other properties. HVI-PAO dimer is prepared as a product or by-product from 1-alkene oligomerization using reduced chromium oxide on solid support.Type: GrantFiled: February 21, 1989Date of Patent: December 15, 1992Assignee: Mobil Oil CorporationInventors: Thomas R. Forbus, Bruce P. Pelrine
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Patent number: 5171916Abstract: Alkylated aromatic functional fluids are prepared by alkylating a light cycle oil with an alkylating agent, such as an alpha C.sub.14 -olefin or coker gas oil, over a crystalline metallosiicate catalyst, preferably an aluminosilicate, including MCM-22, USY or an acid treated kaolin clay. The process produces an improved light cycle oil in which the heteroatom content of the oil is reduced and a high quality synthetic alkylated aromatic functional fluid base stock boiling above 600.degree. F. The reactor temperature can be elevated to increase the functional fluid yield and the extent of heteroatom removal.Type: GrantFiled: June 14, 1991Date of Patent: December 15, 1992Assignee: Mobil Oil Corp.Inventors: Quang N. Le, Michael S. Sarli
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Patent number: 5157186Abstract: A process of using a catalyst composition having enhanced effectiveness in coupling an alkene with an aromatic hydrocarbon having an active hydrogen on a saturated .alpha.-carbon is accomplished with a catalyst obtained by treating an alkali metal with an alkali metal carbonate.Type: GrantFiled: January 13, 1992Date of Patent: October 20, 1992Assignee: Ethyl CorporationInventors: James S. Staton, Michael D. Standiford, David A. Rockstraw
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Patent number: 5043508Abstract: Relatively long chain alkyl aromatic compounds are prepared by alkylating an alkylatable aromatic compound with a relatively long chain alkylating agent under alkylation reaction conditions in the presence of a layered material as an alkylation catalyst. The layered material contains titanate in the layers and oxide pillars separating the layers. The layers also contain vacancies and/or metals incorporated therein. The degree of alkylation is a function of the interplanar d-spacing of the pillared material, which is, in turn a function of the chain length of the swelling agent used to prepare the layered material.Type: GrantFiled: February 23, 1990Date of Patent: August 27, 1991Assignee: Mobil Oil CorporationInventors: Brent A. Aufdembrink, Charles T. Kresge, Quang N. Le, Joosup Shim, Stephen S. Wong
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Patent number: 5034161Abstract: A method for preparation of aryl-substituted aliphatic hydrocarbons is disclosed. The method comprises reacting in the presence of a solid superacid resin catalyst an unsaturated aliphatic hydrocarbon in liquid form with an aromatic hydrocarbon that is susceptible to Friedel-Crafts reaction. The reaction between the liquid unsaturated aliphatic hydrocarbon and the aromatic hydrocarbon produces a reaction product comprising an aryl-substituted aliphatic hydrocarbon.Type: GrantFiled: July 18, 1988Date of Patent: July 23, 1991Assignee: Petrolite CorporationInventor: Bernardus A. O. Alink
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Patent number: 5034563Abstract: Long chain alkyl substituted naphthalenes are produced by the alkylation of naphthalene with an olefin or other alkylating agent possessing at least 6 carbon atoms, usually 12 to 20 carbon atoms, in the presence of an alkylation catalyst comprising a zeolite which contains cations having a radius of at least 2.5 .ANG.. Cations of this size may be provided by hydrated cations such as hydrated ammonium, sodium or potassium cations or by organoammonium cations such as tetraalkylammonium cations. The zeolite is usually a large pore size ze USY. The presence of the bulky cations in the zeolite increases the selectivity of the catalyst for the production of long chain mono-alkyl substituted naphthalenes in preference to more highly substituted products.Type: GrantFiled: April 6, 1990Date of Patent: July 23, 1991Assignee: Mobil Oil CorporationInventors: Henry Ashjian, Quang N. Le, David O. Marler, Joosup Shim, Stephen S. Wong
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Patent number: 5026933Abstract: A process for producing substantially linear hydrocarbons by oligomerizing a lower olefin at elevated temperature and pressure which comprises contacting the lower olefin under oligomerization/polymerization conditions with siliceous acidic ZSM-23 zeolite having Bronsted acid activity; wherein the zeolite has acidic pore activity and wherein the zeolite surface is rendered substantially inactive for acidic reactions. The zeolite surface can be neutralized by a bulky pyridine compound having an effective cross-section larger than the zeolite pore. The preferred deactivating agent is 2,4,6-collidine, which may be applied to the zeolite as a pretreatment or added with olefin feed in a continuous process. The olefin oligomers may be used as alkylating agents to prepare biodegradable alkylbenzenes and alkylphenylsulfonates. A preferred catalyst for this alkylation reaction is dealuminized mordenite.Type: GrantFiled: July 18, 1989Date of Patent: June 25, 1991Assignee: Mobil Oil CorporationInventors: David A. Blain, Nancy M. Page, Lewis B. Young
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Patent number: 5019662Abstract: A process for the production of hydrocarbon white oil by means of hydrogenating a heavy aromatic alkylate is disclosed. The process is characterized in that its feedstock is a previously undesired heavy hydrocarbon byproduct of aromatic alkylation. A white oil derived from such a process has good color and odor properties and results in a superior white oil lubricant.Type: GrantFiled: February 23, 1990Date of Patent: May 28, 1991Assignee: UOPInventors: Bipin V. Vora, Dusan J. Engel
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Patent number: 5012021Abstract: An improved process for the production of alkylaromatic hydrocarbons is disclosed. Paraffinic hydrocarbons are dehydrogenated to yield an olefin-containing stream, which is later charged to an alkylation zone for reaction with an aromatic hydrocarbon in the presence of a solid alkylation catalyst. The olefin-containing stream is first passed through a selective hydrogenation zone in which diolefins are converted to monoolefins by contact with a selective catalyst. This increases the yield and the quality of the product alkylate by greatly reducing the production of biphenyl compounds and oligomers in the alkylation zone. Process efficiency is improved by passing unconverted paraffinic and monoolefinic hydrocarbons from the alkylation zone through another hydrogenation zone for the saturation of monoolefinic hydrocarbons and recycling the saturated stream to the dehydrogenation zone.Type: GrantFiled: September 18, 1990Date of Patent: April 30, 1991Assignee: UOPInventors: Bipin V. Vora, Paul R. Cottrell
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Patent number: 4990718Abstract: A process is disclosed for the production of novel monoalkylbenzenes or substituted benzenes by aromatics alkylation wherein the alkylation catalyst is an acidic shape selective metallosilicate catalyst and the alkylating agent is the olefins dimer by-product of the oligomerization of alpha-olefins in contact with reduced valence state solid chromium oxide catalyst on a porous support. The alkylated benzenes produced comprise those mono-alkylbenzenes wherein the alkyl group contains 12 to 28 carbon atoms and have high viscosity index, low pour point and low viscosity. They have a low degree of residual olefinic unsaturation and are useful as additives to thermally and oxidatively stabilize lubricant materials. The process comprises reacting benzene or substituted benzene with C.sub.6 -C.sub.14 alpha-olefin olefinic dimer having a branch ratio of less than 0.19, or mixture of said dimers, in contact with acidic shape selective zeolite catalyst having large pore size.Type: GrantFiled: April 3, 1989Date of Patent: February 5, 1991Assignee: Mobil Oil CorporationInventor: Bruce P. Pelrine
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Patent number: 4959491Abstract: A two-step dimerization process for producing semi-linear C.sub.12 olefins using homogeneous dimerization catalysts and new C.sub.12 olefins mixtures. The C.sub.12 product is especially useful for the production of biodegradable sulfonated alkylaryl detergents and intermediates therefor.Type: GrantFiled: March 11, 1987Date of Patent: September 25, 1990Assignee: Chevron Research CompanyInventor: Richard S. Threlkel
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Patent number: 4731497Abstract: H-mordenite has been shown to be unique in its ability to yield a high percentage of para-substitution of monoalkyl benzene by alkylation with long chain alpha-olefins. The process also yields a high percentage of substitution of the alpha-olefin in the 2-carbon position. Minimal side effects, such as dialkylation and transalkylation, are also advantages of the process.Type: GrantFiled: December 29, 1986Date of Patent: March 15, 1988Assignee: Atlantic Richfield CompanyInventor: Roger A. Grey
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Patent number: 4714794Abstract: A synthetic oil having excellent oxidation stability, comprising a mixture of monoalkylnaphthalenes which have each a secondary alkyl group of 6 to 24 carbon atoms and in which the specific molar ratio of .alpha.- to .beta.-substituted monalkylnaphthalenes is at least 1.0. The synthetic oil is useful as a thermal medium oil or as the main component of a synthetic lubricating oil.Type: GrantFiled: May 15, 1987Date of Patent: December 22, 1987Assignee: Nippon Oil Co., Ltd.Inventors: Toshio Yoshida, Harumichi Watanabe
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Patent number: 4691068Abstract: An improved process for producing a mono alkyl aromatic by reacting a mono nuclear aromatic compound and an alkylating agent under alkylation conditions to produce the reaction product comprising unreacted mono nuclear aromatic compound, alkane, mono alkyl aromatic, dialkyl aromatic and by-products, treating the reaction product to remove unreacted mono nuclear aromatic compound, free paraffin, and produce a crude product stream containing mono alkyl aromatic, dialkyl aromatic and by-products, separating the majority of the mono alkyl aromatic from the crude product stream to produce a higher boiling fraction containing a minor amount of mono alkyl aromatic, dialkyl aromatic and by-products, and separating the higher boiling fraction into a recycle stream containing mono alkyl aromatic and a by-product stream substantially free of mono alkyl aromatic, and introducing the recycle stream into the alkylation reaction.Type: GrantFiled: August 1, 1986Date of Patent: September 1, 1987Assignee: Vista Chemical CompanyInventor: Kyle W. Resh
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Patent number: 4665275Abstract: A thermal medium oil comprising at least one monosubstituted naphthalene derivative such as .beta.-(1,1-dimethyloctyl) naphthalene, .beta.-(1,1-dimethylhexyl) naphthalene and 2-t.-amylnaphthalene.Type: GrantFiled: June 17, 1985Date of Patent: May 12, 1987Assignee: Nippon Oil Co., Ltd.Inventors: Toshio Yoshida, Harumichi Watanabe
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Patent number: 4604491Abstract: Synthetic base oils for functional fluids and greases are provided comprising a mixture of monoalkylated naphthalenes and polyalkylated naphthalenes, said naphthalenes represented by the formula: ##STR1## wherein the R' groups are independently selected from H and methyl, the monoalkylated naphthalenes have three R groups which are H and one R group which is a 12-26 carbon alkyl, the polyalkylated naphthalenes have from two to four R groups which are 12-26 carbon alkyl and any remainder R groups H, and the weight ratio of monoalkylated naphthalenes to polyalkylated naphthalenes is from 5:95 to 70:30 when the average alkyl group is C.sub.12 -C.sub.16 and from 5:95 to 99:1 when the average alkyl group is C.sub.17 -C.sub.26. In the preferred mixture, the polyalkylated naphthalenes have a numerical ratio of .alpha./.beta. substitution of from 50/50 to 10/90 when the R' groups are both H.Type: GrantFiled: November 26, 1984Date of Patent: August 5, 1986Assignee: Koppers Company, Inc.Inventors: Hans Dressler, Albert A. Meilus
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Patent number: 4570027Abstract: Aromatic molecules are alkylated using a silica-alumina catalyst derived from zeolite. The silica-alumina catalyst is a partially collapsed zeolite, i.e., a material of reduced crystallinity. The alkylation process which employs this material of reduced crystallinity is characterized by a high level of selectivity for the production of monoalkylated product.Type: GrantFiled: April 27, 1984Date of Patent: February 11, 1986Assignee: Exxon Research and Engineering Co.Inventors: Heather A. Boucher, Ian A. Cody
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Patent number: 4567312Abstract: Paraffins having a carbon number in excess of 10 are converted to aromatics, such as n-alkylbenzenes, over a dehydrocyclization catalyst comprising a large-pore zeolite containing at least one Group VIII metal. This process is carried out at a pressure of less than 100 psig. The dehydrocyclization catalyst can contain an alkaline earth metal selected from the group consisting of barium, strontium, and calcium. Preferably, the dehydrocyclization catalyst has from 8 to 10 percent by weight barium and from 0.2 to 1.0 percent by weight platinum, and the large-pore zeolite is a type L zeolite.Type: GrantFiled: January 25, 1984Date of Patent: January 28, 1986Assignee: Chevron Research CompanyInventors: Stephen J. Miller, Sue D. Pandey
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Patent number: 4559131Abstract: A process is provided for using a reactivated catalyst composition comprising a crystalline zeolite material having a silicon/aluminum atomic ratio of at least about 3.5, said catalyst composition having been deactivated by contact with steam. The reactivation method involves the necessary steps of contacting said steam-deactivated catalyst composition with a metal salt solution, followed by contacting said metal salt solution contacted catalyst composition with an aqueous ammonium ion-containing solution.Type: GrantFiled: July 16, 1984Date of Patent: December 17, 1985Assignee: Mobil Oil CorporationInventor: Joseph N. Miale
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Patent number: 4523048Abstract: An improved process for the production of alkylaromatic hydrocarbons is disclosed. Paraffinic hydrocarbons are dehydrogenated to yield an olefin-containing stream, which is later charged to an alkylation zone for reaction with an aromatic hydrocarbon. The olefin-containing stream is first passed through a selective hydrogenation zone in which diolefins are converted to monoolefins by contact with a selective catalyst. This increases the yield and the quality of the product alkylate by greatly reducing the production of biphenyl compounds and oligomers in the alkylation zone. The selective hydrogenation zone is located between the vapor-liquid separator and stripper column of the dehydrogenation zone.Type: GrantFiled: April 4, 1984Date of Patent: June 11, 1985Assignee: UOP Inc.Inventor: Bipin V. Vora
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Patent number: 4503277Abstract: A process is disclosed for the production of alkylaromatic hydrocarbons by the HF-catalyzed reaction of an aromatic hydrocarbon with a C.sub.8 -plus acyclic olefin. The production of linear alkylbenzenes is preferred. The HF is regenerated in a regeneration column in which high boiling compounds are removed from the HF fed to the column. The main stream of HF enters an upper intermediate point in the regeneration column. A second portion of the HF is fed to the top of the regeneration column as reflux. This second portion of HF is withdrawn from the reaction zone rather than from the overhead receiver of the HF regeneration column as in the prior art regeneration method.Type: GrantFiled: November 30, 1983Date of Patent: March 5, 1985Assignee: UOP Inc.Inventor: James F. Himes
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Patent number: 4463205Abstract: A process is disclosed for the production of alkylaromatic hydrocarbons by the alkylation of an aromatic hydrocarbon, such as benzene, with a C.sub.8 -plus acyclic olefin which preferably is a normal olefin. The hydrocarbonaceous effluent of the alkylation reaction zone is separated by fractional distillation to yield both a product stream containing monoalkylated aromatics and a small bottoms stream containing dialkylated aromatics and other high boiling compounds but which is substantially devoid of the product monoalkylated aromatics. The product stream is a portion of a sidecut stream withdrawn from the first of two vacuum columns, with a second portion of the sidecut being passed into the second column. The bottoms stream of the first column is also passed into the second column and the overhead vapor of the second column enters an upper portion of the first column.Type: GrantFiled: September 2, 1983Date of Patent: July 31, 1984Assignee: UOP Inc.Inventor: Joel B. Spinner
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Patent number: 4358628Abstract: Benzene compounds are successfully alkylated with detergent range olefins with a very active and very selective catalyst prepared by impregnating a 70-90% silica support with a tungsten salt, calcining the impregnated material and subsequently activating the catalyst in a neutral or reducing atmosphere at a temperature ranging from about 200.degree. C. to about 350.degree. C.Type: GrantFiled: June 26, 1981Date of Patent: November 9, 1982Assignee: Shell Oil CompanyInventor: Lynn H. Slaugh
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Patent number: 4329509Abstract: A process for the co-production of 2-alkanones having at least five carbon atoms and phenol or a substituted phenol. In the first step, benzene or a substituted benzene is alkylated with an alkyl moiety of at least five carbon atoms to selectively produce the 2-arylalkane isomer. Subsequent oxidation to the hydroperoxide and acid cleavage thereof yields the desired product. The alkylation step is carried out in the presence of a novel class of selective crystalline zeolite materials having pore openings with a major dimension of six to seven angstroms.Type: GrantFiled: January 22, 1981Date of Patent: May 11, 1982Assignee: Mobil Oil CorporationInventors: Werner O. Haag, Lewis B. Young
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Patent number: 4301316Abstract: A process for the selective alkylation of substituted or unsubstituted benzene compounds with relatively long chain length alkylating agents to produce phenylalkanes having an improved yield of the more external phenyl isomers. The reaction is carried out in the presence of crystalline zeolite catalysts, such as ZSM-4, ZSM-20, ZSM-38, mazzite, Linde Type L and zeolite Beta.Type: GrantFiled: November 20, 1979Date of Patent: November 17, 1981Assignee: Mobil Oil CorporationInventor: Lewis B. Young
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Patent number: 4301317Abstract: A process for the selective alkylation of substituted or unsubstituted benzene compounds with relatively long chain length alkylating agents to produce phenylalkanes having an improved yield of the 2-phenylkane isomer. The reaction is carried out in the presence of crystalline zeolite catalysts characterized by channels or networks of pores having openings with a major dimension of 6-7 angstroms.Type: GrantFiled: November 20, 1979Date of Patent: November 17, 1981Assignee: Mobil Oil CorporationInventor: Lewis B. Young
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Patent number: 4255343Abstract: Process for preparing 2-t-alkylanthracene, which process comprises contacting and reacting, with good mixing, at a temperature of at least 110.degree. C., anthracene and a branched-chain alkylating agent, the alkylating moiety of which contains at least four carbon atoms, in the presence of a catalyst selected from hydrocarbonsulfonic acids which are free of nonaromatic unsaturation, organic carboxylic acids having a K.sub.a of 0.6 to 0.001, acid zeolites, amorphous silica-aluminas, and polymeric arenesulfonic acid resins, to give a product mixture of which the major constituent is 2-t-alkylanthracene.Type: GrantFiled: August 13, 1979Date of Patent: March 10, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Lawrence W. Gosser
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Patent number: 4238343Abstract: A synthetic oil useful as an insulating fluid in electrical apparatus is prepared by reacting an aromatic compound with the oligomers of four to 12 carbon alpha-olefins containing predominantly at least about 30 carbon atoms up to about 60 carbon atoms. A synthetic insulating oil for electrical power transformers is prepared by reacting benzene in a 1:1 molar ratio with a tetramerpentamer mixture obtained by the oligomerization of 1-decene.Type: GrantFiled: October 26, 1978Date of Patent: December 9, 1980Assignee: Gulf Research & Development CompanyInventor: John P. Pellegrini, Jr.
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Patent number: 4216345Abstract: Process for the preparation of alkylbenzenes by partial chlorination of linear C.sub.9 -C.sub.15 paraffins, catalytic alkylation of benzene with the resulting mixture and fractionation by distillation of the alkylation products.At least a part of the unreacted paraffins recovered by fractionation and to be recycled to the chlorination stage is submitted, continuously or intermittently, to a purification treatment with molecular sieves.The content in undesired by-products of the alkylbenzenes can thus be maintained at negligibly low values.Type: GrantFiled: September 28, 1978Date of Patent: August 5, 1980Assignee: Euteco S.p.A.Inventors: Giuseppe Messina, Loreno Lorenzoni, Lucio Di Fiore
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Patent number: 4211665Abstract: Electrical apparatus containing a novel synthetic oil as an insulating fluid which is prepared by reacting an aromatic compound with the oligomers of four to 12 carbon alpha-olefins containing predominantly at least about 30 carbon atoms up to about 60 carbon atoms. For example, an electrical power transformer is provided containing a synthetic insulating oil prepared by reacting benzene in a 1:1 molar ratio with a tetramer-pentamer mixture obtained by the oligomerization of 1-decene.Type: GrantFiled: October 26, 1978Date of Patent: July 8, 1980Assignee: Gulf Research and Development CompanyInventor: John P. Pellegrini, Jr.
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Patent number: 4197417Abstract: Manufacture of o-benzyltoluenes by reaction of a benzyl halide of formula ##STR1## with a compound of formula ##STR2## at 50.degree. to 250.degree. C., one of R and R.sup.1 being methyl and the other H or methyl, and adding the compound II to a mixture of III with a small amount of iron or iron compound.Type: GrantFiled: September 5, 1978Date of Patent: April 8, 1980Assignee: Imperial Chemical Industries LimitedInventor: John O. Morley
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Patent number: 4197413Abstract: A four-step method for the selective production of the 1,3-isomer of methylphenol comprising the alkylation of toluene with propylene in the presence of a specified type of zeolite alkylation catalyst followed by the selective reaction, via a specified type of shape selective zeolite, of the 1,4-isomer of the alkylation product to leave the 1,3-isomer thereof in excess of equilibrium. Subsequent oxidation and acid catalyzed rearrangement results in desirably high yield of 3-methylphenol.Type: GrantFiled: December 14, 1978Date of Patent: April 8, 1980Assignee: Mobil Oil CorporationInventors: Warren W. Kaeding, Margaret M. Wu, Lewis B. Young, George T. Burress
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Patent number: 4194058Abstract: Process for the conversion of aromatic hydrocarbons. Especially useful for the reaction of an alkylating agent, preferably propylene, with an aromatic hydrocarbon. Novel feature is the use of a catalyst comprising nickel, molybdenum, platinum and a zeolitic carrier material.Type: GrantFiled: December 26, 1978Date of Patent: March 18, 1980Assignee: UOP Inc.Inventor: Lee Hilfman
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Patent number: 4180691Abstract: An improved process for the acid-catalyzed alkylation of C.sub.6 to C.sub.9 aromatic hydrocarbons with olefins to produce linear alkylaromatic hydrocarbons useful as detergent precursors. The alkylation reaction is performed in the presence of a surfactant to reduce the 2-phenyl isomer content of the product linear alkylaromatic hydrocarbons.Type: GrantFiled: August 4, 1978Date of Patent: December 25, 1979Assignee: UOP Inc.Inventor: George E. Illingworth