Preparing By Dehydration Of An Organic Hydroxy Containing Compound (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/698)
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Patent number: 5444168Abstract: Secondary alcohols are converted to symmetrical secondary alkyl ethers in high selectivity. The method employs acidic solid metallosilicate catalyst particles to accomplish the etherification by selective intermolecular dehydration of secondary alcohol to form di-secondary alkyl ethers. Preferably, the catalysts are solid shape selective aluminosilicate particles, especially zeolite such as ZSM-5, zeolite HY and zeolite Beta. Continuous separation of by-product olefin and ether during the etherification reaction improves selectivity.Type: GrantFiled: May 16, 1994Date of Patent: August 22, 1995Assignee: Mobil Oil CorporationInventor: Stephen H. Brown
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Patent number: 5436376Abstract: A plural stage process for the production of tertiary butyl alcohol from isobutane wherein isobutane is reacted with oxygen in a first reactor to prepare a primary liquid reaction mixture comprising unreacted isobutane, tertiary butyl alcohol, tertiary butyl hydroperoxide and small amounts of oxygen-containing by-products, distilling the primary reaction product to provide a first lighter isobutane recycle distillation fraction and a first heavier liquid distillation fraction comprising the debutanized mixture of tertiary butyl hydroperoxide with tertiary butyl alcohol, diluting the first heavier liquid distillation fraction with an amount of tertiary butyl alcohol sufficient to provide a feed mixture comprising about 15 to 25 wt. % of tertiary butyl hydroperoxide, about 75 to 85 wt.Type: GrantFiled: August 11, 1994Date of Patent: July 25, 1995Assignee: Texaco Chemical Inc.Inventors: Yu-Hwa E. Sheu, John R. Sanderson, Mark A. Mueller, William A. Smith
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Patent number: 5430198Abstract: Disclosed is a two-step process for the generation of diisopropyl ether from a crude by-product acetone stream which comprises:a) Hydrogenating said crude acetone over a bulk-metal, nickel-rich catalyst to give an isopropanol-rich effluent;b) Dehydrating said isopropanol-rich intermediate in the presence of a strong acid zeolite catalyst from the group consisting of .beta.-zeolite, optionally modified with one or more metals from Group IB, VB, VIB, VIIB and VIII of the Periodic Table, and a dealuminized Y-zeolite, wherein the dehydration temperature is from about 80.degree. C. to 200.degree. C.Type: GrantFiled: November 8, 1993Date of Patent: July 4, 1995Assignee: Texaco Chemical Inc.Inventors: John F. Knifton, Pei-Shing E. Dai
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Patent number: 5424458Abstract: The present invention provides a novel integration of an existing MTBE process unit with new propylene oxide producing facilities whereby through this integration new propylene oxide production is achieved without significant increase in MTBE production.Type: GrantFiled: March 8, 1994Date of Patent: June 13, 1995Assignee: Arco Chemical Technology, L.P.Inventors: Gordon A. Sullivan, Herry E. Eilerts-de Haan, William J. Piel, John J. Leonard
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Patent number: 5395982Abstract: An impure methyl tertiary butyl ether product contaminated with isobutylene, methanol and water is purified by continuous counter-current contact with water and isobutylene in a counter-current contact extraction tower to provide an overhead extract comprising isobutylene, methyl tertiary butyl ether and water and a raffinate comprising methanol, water and a minor amount of methyl tertiary butyl ether, the overhead raffinate being separated in a methyl tertiary butyl ether purification distillation zone into a lighter distillation fraction comprising isobutylene and water and a heavier distillation fraction consisting essentially of methyl tertiary butyl ether, the lighter distillation fraction being decanted to remove water and to provide a distillate isobutylene fraction that is charged to a surge drum from which isobutylene is returned to the contact tower.Type: GrantFiled: November 5, 1993Date of Patent: March 7, 1995Assignee: Texaco Chemical CompanyInventors: John R. Cassata, Stuart J. Parker, Rei-Yu J. Hwan, Catherine J. Conkwright
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Patent number: 5387722Abstract: Disclosed is a process for preparing alkyl tertiary alkyl ethers in one step which comprises reacting tert-butanol and a C.sub.1 -C.sub.4 primary alcohol in the presence of a catalyst consisting essentially of a pentasil zeolite having a silica/alumina ratio of 50-150, optionally with a binder at a temperature of about 80.degree. to 200.degree. C. and atmospheric pressure to about 1000 psig, wherein when the temperature is in the operating range above 140.degree. C., the product comprises a two-phase mix of a MTBE or ETBE and isobutylene product-rich phase and a heavier aqueous primary alcohol-rich phase.Type: GrantFiled: September 23, 1993Date of Patent: February 7, 1995Assignee: Texaco Chemical Inc.Inventors: John F. Knifton, Pei-Shing E. Dai
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Patent number: 5387721Abstract: Methyl tertiary butyl ether (MTBE) is formed by reaction of methanol with tertiary butyl ether in two catalyst beds. A feedstock mixture comprising methanol and tertiary butyl alcohol in a molar ratio of 2 to 3 moles of methanol per mole of tertiary butyl alcohol is reacted in a first etherification reaction zone at a liquid hourly space velocity of 1 to 10 volumes of feedstock mixture per volume of catalyst per hour. A first reaction product mixture is fractionated to remove unreacted methanol, isobutylene and MTBE overhead. This isobutylene is passed to a second etherification reaction zone at a liquid hourly space velocity of 1 to 10. A second reaction product mixture is fractionated to recover additional MTBE.Type: GrantFiled: December 21, 1993Date of Patent: February 7, 1995Assignee: Texaco Inc.Inventors: Charles J. Kruse, Kyle L. Preston, Brian L. Benac
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Patent number: 5387723Abstract: Disclosed is a method for producing alkyl tertiary alkyl ethers which comprises reacting t-butanol with an alkanol in the presence of a catalyst which exhibits extended life comprising .beta.-zeolite modified with one or more metals selected from the group consisting of Group IA and Group IIIB of the Periodic Table and continuously contacting said alkanol and t-butanol in a molar amount from about 10:1 to 1:10 over said zeolite catalyst at a temperature of about 20.degree. C. to about 250.degree. C. and a pressure of about atmospheric to about 1000 psig.Type: GrantFiled: January 12, 1994Date of Patent: February 7, 1995Assignee: Texaco Chemical Inc.Inventors: John F. Knifton, Pei-Shing E. Dai
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Patent number: 5386065Abstract: Methyl tertiary butyl ether (MTBE) is formed by reaction of methanol with tertiary butyl ether in two catalyst beds. A feedstock mixture comprising methanol and tertiary butyl alcohol in a molar ratio of 2 to 3 moles of methanol per mole of tertiary butyl alcohol is reacted in a first etherification reaction zone at a liquid hourly space velocity of 1 to 10 volumes of feedstock mixture per volume of catalyst per hour. A first reaction product mixture is fractionated to remove MTBE as an overhead fraction. The bottoms fraction comprising unreacted methanol and tertiary butyl alcohol is passed to a second etherification reaction zone at a liquid hourly space velocity of 0.5 to 4. A second reaction product mixture is fractionated to recover additional MTBE.Type: GrantFiled: December 21, 1993Date of Patent: January 31, 1995Assignee: Texaco Inc.Inventors: Charles J. Kruse, Kyle L. Preston, Brian L. Benac
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Patent number: 5364980Abstract: A method for preparing unsymmetrical dialkyl ethers and derivatives thereof. The ethers are prepared by reacting a C.sub.1 to C.sub.3 aliphatic alcohol with a tertiary alcohol in the presence of a novel catalyst comprised of a transition metal pillared interlayered clay having generally separated layers wherein the interlayer distances are substantially greater than a precursor of the same but non-separated clay and wherein the product includes multimetallic pillars comprised of a cationic polymeric complex of the formula:Al.sup.iv (Al.sub.12-x M.sub.x).sup.vi O.sub.4 (OH).sub.24.sup.a+where x is a number from 1 to 6; a depends on the selection of M and N; N is selected from Al.sup.3+, Si.sup.4+, Ga.sup.3+, Ge.sup.4+, As.sup.5+, P.sup.5+, Cr.sup.3+, Fe.sup.3+, V.sup.5+, Ru.sup.3+, Ru.sup.4+, N.sup.3+ ; and M is selected from a metal from Groups 5B, 6B, 7B and 8 of the 4th, 5th and 6th Periods of the Periodic Table of the Elements.Type: GrantFiled: December 30, 1991Date of Patent: November 15, 1994Assignee: Exxon Research & Engineering Co.Inventors: Michael C. Kerby, David E. W. Vaughan
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Patent number: 5364981Abstract: Disclosed is an improved process for preparing alkyl tertiary alkyl ethers, especially methyl t-butyl ether, in one step which comprises reacting tertiary butanol and methanol in the presence of a catalyst comprising .beta.-zeolite modified with one or more metals selected from Group VIII of the Periodic Table, and optionally further modified with a halogen or a Group IB metal, with an alumina binder, at a temperature of about 20.degree. C. to 250.degree. C. and atmospheric pressure to about 1000 psig, wherein when the temperature is in the operating range above about 140.degree. C., the product comprises a two-phase mix of an MTBE-isobutylene and, optionally, diisobutylene product-rich phase and a heavier aqueous ethanol-rich phase.Type: GrantFiled: November 8, 1993Date of Patent: November 15, 1994Assignee: Texaco Chemical CompanyInventors: John F. Knifton, Pei-Shing E. Dai
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Patent number: 5364976Abstract: A process for simultaneously producing C.sub.5 -C.sub.12 alkane(s) and C.sub.5 -C.sub.8 tertiary alkyl ether(s) employs a liquid feed mixture containing (a) at least one C.sub.4 -C.sub.7 isoalkane, (b) at least one second reactant which is at least one C.sub.4 -C.sub.8 isoalkane, and/or at least one C.sub.4 -C.sub.8 tertiary alkyl alcohol, and (c) at least one C.sub.1 -C.sub.6 linear alkyl alcohol, wherein the liquid feed mixture is contacted at effective reaction conditions with a catalyst consisting essentially of trifluoromethanesulfonic acid and a specific solid carrier material (preferably alumina).Type: GrantFiled: October 29, 1993Date of Patent: November 15, 1994Assignee: Phillips Petroleum CompanyInventor: Lyle R. Kallenbach
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Patent number: 5354912Abstract: An isobutylene feed mixture comprising MTBE, isobutylene and methanol is passed through an isobutylene conversion zone to form an isobutylene conversion product comprising unreacted methanol, unreacted isobutylene, dimethyl ether, MTBE and water, then charged to a countercurrent methanol extraction zone and contacting with water to provide an overhead raffinate comprising isobutylene, MTBE and water, and an extract comprising methanol, water, MTBE, isobutylene and dimethyl ether;the extract is distilled to provide a vaporized overhead fraction comprising MTBE, isobutylene, methanol, and dimethyl ether;the vaporized overhead fraction is partially condensed and from about 5 to 10 wt. % of the mixed phase condensate is vented to thereby provide a liquid condensate that is substantially free from dissolved dimethyl ether, and the condensate is recycled to the methanol extraction zone.Type: GrantFiled: June 1, 1993Date of Patent: October 11, 1994Assignee: Texaco Chemical CompanyInventors: Rei-Yu J. Hwan, Charles J. Kruse
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Patent number: 5352847Abstract: A method is disclosed wherein t-butanol is reacted with methanol in a reaction zone in one step to provide methyl tert-butyl ether and the improvement of accomplishing the reaction which comprises:a. Using a catalyst comprising a chlorohydrol-treated, phosphated montmorillonite clay,b. continuously contacting said t-butanol and methanol in a molar amount of about 0.1 to 10 moles of methanol per mole of t-butanol with said catalyst at a temperature of about 20.degree. C. to about 250.degree. C. and a pressure of about atmospheric to about 1000 psig to obtain the methyl tert-butyl ether product.Type: GrantFiled: September 27, 1993Date of Patent: October 4, 1994Assignee: Texaco Inc.Inventor: John F. Knifton
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Patent number: 5349094Abstract: Oligoglycerol mixtures having a high diglycerol content are prepared by a process in which glycerol is condensed in the presence of zeolites corresponding to formula (I)M.sub.2/z O * Al.sub.2 O.sub.3 * x SIO.sub.2 * y H.sub.2 O (I)in which M is an alkali metal or alkaline earth metal having a valency of z, x is a number of 1.8 to 12 and y is a number of 0 to 8. The water of condensation which is formed during the reaction, is continuously removed from the reaction mixture and the reaction is terminated when the quantity of water theoretically necessary for the formation of diglycerol has been separated.Type: GrantFiled: June 12, 1992Date of Patent: September 20, 1994Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Eugene G. Harris, Udo Hees, Reinhard Bunte, Johannes W. Hachgenei, Peter Kuhm
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Patent number: 5338890Abstract: Disclosed is a method wherein t-butanol is reacted with methanol in one step to provide methyl t-butyl ether at a temperature of about 20.degree. C. to 250.degree. C. and a pressure of about atmospheric to about 1000 psig employing a heterogenous catalyst comprising a Group IV oxide having an alkylsulfonic acid covalently bonded thereto, particularly alkylsulfonic acid covalently bonded to silica gel and having the structure: ##STR1## wherein R is an alkyl group having from 1 to 3 carbon atoms and n is an integer in the range of 3 to 10.Type: GrantFiled: July 19, 1993Date of Patent: August 16, 1994Assignee: Texaco Chemical CompanyInventors: John F. Knifton, John R. Sanderson
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Patent number: 5316627Abstract: This invention relates to a process for producing odourless dimethyl ether (DME) which is thus an excellent propellant. This dimethyl ether is produced from methanol, the methanol feed, prior to the reaction to form dimethyl ether, and/or the dimethyl ether product still containing odorants being treated with acidic materials, preferably acidic ion exchangers.Type: GrantFiled: October 1, 1992Date of Patent: May 31, 1994Assignee: RWE-DEA Aktiengesellschaft fuer Mineraloel und ChemieInventor: Hartmut Hammer
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Patent number: 5313006Abstract: Disclosed is an improvement in a method for cogeneration of isobutylene and MTBE by etherification of tBA/MeOH over an ion-exchange resin which allows for more complete conversion of the remaining tBA fraction and comprises a second step consisting essentially of recovering the MTBE from the primary fractionator as an overhead fraction and etherifying the bottoms from the primary fractionator over an inorganic acid catalyst comprising a crystalline aluminosilicate faujasite-type Y-zeolite modified with a compound selected from a fluoride-containing compound including hydrofluoric acid, ammonium fluoride, fluorosulfonic acids and their cogeners and triflic anhydride at a temperature of greater than 120.degree. C.Type: GrantFiled: December 21, 1992Date of Patent: May 17, 1994Assignee: Texaco Chemical CompanyInventor: John F. Knifton
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Patent number: 5300697Abstract: A method is disclosed wherein t-butanol is reacted with methanol in a reaction zone in one step to provide methyl tert-butyl ether and the improvement of accomplishing the reaction which comprises:a. Using a catalyst consisting of a crystalline aluminosilicate faujasite Y-type zeolite which has been treated with hydrogen fluoride;b. continuously contacting said t-butanol and methanol in a molar amount of about 0.1 to 10 moles of methanol per mole of t-butanol with said catalyst at a temperature of about 20.degree. C. to about 250.degree. C. and a pressure of about atmospheric to about 1000 psig to obtain the methyl tert-butyl ether product wherein the product mix separates into an isobutylene-MTBE product-rich phase and a heavier aqueous methanol phase.Type: GrantFiled: December 7, 1992Date of Patent: April 5, 1994Assignee: Texaco Chemical CompanyInventors: John F. Knifton, John R. Sanderson
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Patent number: 5292964Abstract: The present invention provides a process for the preparation of MTBE or ETBE wherein TBA is reacted with methanol or ethanol and an effluent is formed which contains the water of etherification and at least 1 mol lower alcohol per 2 mols MTBE or ETBE, this effluent is distilled to separate an overhead of lower alcohol and ether from a bottoms containing the water of reaction, and a lower alcohol/ether admixture from the overhead is reacted with isobutylene to form additional quantities of MTBE or ETBE.Type: GrantFiled: November 16, 1992Date of Patent: March 8, 1994Assignee: Arco Chemical Technology, L.P.Inventor: Vijai P. Gupta
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Patent number: 5254749Abstract: The present invention relates to a process for producing dipentaerythritol through the dehydration condensation of pentaerythritol in the presence of an acid catalyst. This production process comprises the step of carrying out the dehydration condensation preferably in the presence of an acid catalyst, and/or the step of lowering the temperature of the reaction mixture before the conversion of pentaerythritol becomes not less than 25%, to stop the reaction so that the concentration of tripentaerythritol formed during the reaction may not be increased, and at the same time to give a reaction mixture containing dipentaerythritol in an increased concentration.Type: GrantFiled: August 9, 1991Date of Patent: October 19, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Yoshihiko Kambara, Toru Idemoto, Yasuki Ono, Chika Tona
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Patent number: 5243102Abstract: Ethers suitable for use as high octane oxygenate additives for motor fuels are produced by a multistage catalytic distillation process wherein a multi-carbon number range olefin feed stream, e.g. C.sub.5 -C.sub.7 isoolefins, is charged to two catalytic distillation zones operated in series. The heavier paraffins and olefins in the olefin feed stream and a first product ether are concentrated into the bottoms stream of the first catalytic distillation zone. This bottoms stream and additional alcohol is passed into the second catalytic distillation zone in which the heavier isoolefin is consumed in the production of a second ether. Preferably a portion of the catalytic distillation zone overhead liquid is passed into an external close coupled adiabatic reactor.Type: GrantFiled: October 1, 1992Date of Patent: September 7, 1993Assignee: UOPInventors: Terry L. Marker, Charles P. Luebke
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Patent number: 5243091Abstract: A method for the preparation of methyl tertiary butyl ether is provided wherein a mixture of methanol and substantially peroxides-free tertiary butyl alcohol are catalytically reacted to form a reaction product that is separated into a first lighter distillation fraction comprising isobutylene, methanol and methyl tertiary butyl ether and a second heavier distillation fraction comprising methanol, tertiary butyl alcohol and water, wherein the first distillation fraction and a first recycle isobutylene fraction are reacted to form an isobutylene conversion product that is charged, together with recycle isobutylene to a methanol extraction zone and countercurrently contacted with water to provide an overhead extract comprising aqueous isobutylene, and wherein the isobutylene is recovered and recycled.Type: GrantFiled: November 19, 1992Date of Patent: September 7, 1993Assignee: Texaco Chemical CompanyInventors: Charles J. Kruse, Rei-Yu J. Hwan, Kyle L. Preston, Feng-Ran Sheu
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Patent number: 5227141Abstract: A membrane catalytic reactor which comprises a heteropolyacid selected from the group consisting of 12-tungstophosphoric acid, 12-molybdophosphoric acid, 12-molybdotungstophosphoric acid, and 12-tungstosilicic acid, and polysulfone membrane is provided. This membrane catalytic reactor is applicable to vapor-phase dehydration, dehydrogenation, oxidation, and simultaneous separation of organic or inorganic materials, particularly vapor-phase dehydration of ethanol.Type: GrantFiled: May 5, 1992Date of Patent: July 13, 1993Assignee: Korea Institute of Science and TechnologyInventors: Jae J. Kim, Wha Y. Lee, In K. Song
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Patent number: 5227538Abstract: A process is provided for the catalytic asymmetric reduction of ketones to provide alcohol reaction products which are enriched in one enantiomer. The asymmetric reduction is accomplished utilizing an achiral metal precatalyst in combination with an optically active additive.Type: GrantFiled: November 14, 1991Date of Patent: July 13, 1993Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Alberto Gutierrez, Robert B. Grossman
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Patent number: 5220078Abstract: A method is disclosed wherein t-butanol is reacted with methanol in a reaction zone in one step to provide methyl tert-butyl ether and the improvement in accomplishing the reaction which comprises:a. Using a catalyst consisting of a crystalline aluminosilicate faujasite Y-type zeolite which has been treated with a fluorophosphoric acid;b. continuously contacting said t-butanol and methanol in a molar amount of about 0.1 to 10 moles of methanol per mole of t-butanol with said catalyst at a temperature of about 20.degree. C. to about 250.degree. C. and a pressure of about atmospheric to about 1000 psig to obtain the methyl tert-butyl ether product.Type: GrantFiled: July 23, 1992Date of Patent: June 15, 1993Assignee: Texaco Chemical CompanyInventors: John F. Knifton, John R. Sanderson
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Patent number: 5214218Abstract: A method is disclosed wherein t-butanol is reacted with methanol in a reaction zone in one step to provide methyl tert-butyl ether and the improvement of accomplishing the reaction which comprises:a. Using a catalyst comprising a montmorillonite clay treated with a haloacid;b. continuously contacting said t-butanol and methanol in a molar amount of about 0.1 to 10 moles of methanol per mole of t-butanol with said catalyst at a temperature of about 20.degree. C. to about 250.degree. C. and a pressure of about atmospheric to about 1000 psig to obtain the methyl tert-butyl ether product.Type: GrantFiled: May 4, 1992Date of Patent: May 25, 1993Assignee: Texaco Chemical CompanyInventor: John F. Knifton
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Patent number: 5183947Abstract: A method is disclosed wherein t-butanol is reacted with methanol in a reaction zone in one step to provide methyl tert-butyl ether and the improvement of accomplishing the reaction which comprises:a. Using a catalyst comprising a montmorillonite clay treated with a fluorophosphoric acid,b. Continuously contacting said t-butanol and methanol in a molar amount of about 0.1 to 10 moles of methanol per mole of t-butanol with said catalyst at a temperature of about 20.degree. C. to about 250.degree. C. and a pressure of about atmospheric to about 1000 psig to obtain the methyl tert-butyl ether product.Type: GrantFiled: June 19, 1992Date of Patent: February 2, 1993Assignee: Texaco Chemical CompanyInventors: John F. Knifton, John R. Sanderson
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Patent number: 5162592Abstract: Disclosed is an improved process for preparing methyl t-butyl ether in one step which comprises reacting tertiary butanol and methanol in the presence of a catalyst comprising a zeolite modified with a metal selected from the group consisting of Groups IB, VB, VIB, VIIB or VIII of the Periodic Table at a temperature of about 20.degree. C. to 250.degree. C. and atmospheric pressure to about 1000 psig, wherein when the temperature is in the operating range above about 160.degree. C., the product comprises a two-phase mix of an isobutylene-MTBE product-rich phase and a heavier aqueous methanol-rich phase.Type: GrantFiled: November 25, 1991Date of Patent: November 10, 1992Assignee: Texaco Chemical CompanyInventors: John F. Knifton, John R. Sanderson, Peishing E. Dai
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Patent number: 5157161Abstract: A method is disclosed wherein t-butanol is reacted with methanol in a reaction zone in the presence of a catalyst to provide methyl-tert-butyl ether and the improvement of accomplishing the reaction in one-step which comprises:a. contacting the reactants with a montmorillonite silica-alumina catalyst which has been treated with hydrogen fluoride;b. continuously contacting said t-butanol and methanol in a molar amount of about 0.1 to 10 moles of methanol per mole of t-butanol with said catalyst at a temperature of about 20.degree. C. to about 250.degree. C. and a pressure of about atmospheric to about 1000 psig to obtain the methyl tert-butyl product, wherein under certain conditions the product mix separates into an isobutylene-MTBE product-rich phase and a heavier aqueous methanol phase.Type: GrantFiled: December 9, 1991Date of Patent: October 20, 1992Assignee: Texaco Chemical CompanyInventor: John F. Knifton
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Patent number: 5157162Abstract: A method is disclosed wherein t-butanol is reacted with methanol in a reaction zone in one step to provide methyl tert-butyl ether and the improvement of accomplishing the reaction which comprises:a. Using a catalyst consisting of a montmorillonite clay, optionally pretreated with a mineral acid, then treated with a fluorosulfonic acid;b. continuously contacting said t-butanol and methanol in a molar amount of about 0.1 to 10 moles of methanol per mole of t-butanol with said catalyst at a temperature of about 20.degree. C. to about 250.degree. C. and a pressure of about atmospheric to about 1000 psig to obtain the methyl tert-butyl ether product.Type: GrantFiled: October 25, 1991Date of Patent: October 20, 1992Assignee: Texaco Chemical CompanyInventor: John F. Knifton
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Patent number: 5157163Abstract: A method for the separation of methanol from MTBE contained in a reaction mixture comprising water, methanol, TBA and MTBE which comprises distilling the reaction mixture in the presence of added water in order to provide a distillate fraction containing most of the MTBE and a heavier distillation fraction containing most of the tertiary-butanol, water and methanol charged to the distillation column.Type: GrantFiled: October 3, 1991Date of Patent: October 20, 1992Assignee: Texaco Chemical CompanyInventors: William A. Smith, Roya Tooloian
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Patent number: 5144086Abstract: A process for synthesizing di-isopropyl ether (DIPE) by etherification of isopropanol. A multi-stage process can employ propene in mixture with other feedstock materials, such as propane from refinery gas, in a primary hydration stage to produce isopropanol. The isopropanol is enriched between stages to remove water. In the second reaction stage the isopropanol is converted catalytically with large pore acidic zeolite to yield DIPE, which can be separated to recover pure propene.Type: GrantFiled: May 6, 1991Date of Patent: September 1, 1992Assignee: Mobil Oil CorporationInventors: Mohsen N. Harandi, Werner O. Haag, Hartley Owen, Weldon K. Bell
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Patent number: 5102428Abstract: A process is disclosed for integrating etherification to produce diisopropyl ether (DIPE) with processes to convert oxygenates and hydrocarbons to gasoline boiling range hydrocarbons in a manner which eliminates the requirement to recycle unreacted C.sub.3 hydrocarbons to the DIPE etherification zone. In the novel integrated process the unreacted C.sub.3 hydrocarbons are separated as vapor and passed to a conversion zone in contact with acidic metallosilicate catalyst. Depending on the conversion conditions the unreacted C.sub.3 hydrocarbons are converted to gasoline, distillate and/or aromatics, preferably in conjunction with additional feedstock containing lower oxygenates, olefins or paraffins. Also, isopropanol (IPA) and minor by-product dimers and trimers of propene from the DIPE reaction are separated and passed as a feedstream to the oxygenates and hydrocarbon conversion zone.Type: GrantFiled: October 20, 1989Date of Patent: April 7, 1992Assignee: Mobil Oil CorporationInventors: Hartley Owen, Mohsen N. Harandi
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Patent number: 5099072Abstract: A method is disclosed wherein t-butanol is reacted with methanol in a reaction zone in the presence of a catalyst to provide methyl-tert-butyl ether and the improvement of accomplishing the reaction in one-step which comprises:a. using an acidic montmorillonite silica-alumina catalyst;b. continuously contacting said t-butanol and methanol in a molar amount of about 0.1 to 10 moles of methanol per mole of t-butanol with said catalyst at a temperature of about 20.degree. C. to about 250.degree. C. and a pressure of about atmospheric to about 1000 psig to obtain the methyl-tert-butyl product.Type: GrantFiled: March 16, 1990Date of Patent: March 24, 1992Assignee: Texaco Chemical CompanyInventor: John F. Knifton
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Patent number: 5081318Abstract: A method is disclosed wherein t-butanol is reacted with methanol in a reaction zone in one step to provide methyl tert-butyl ether and the improvement of accomplishing the reaction which comprises:a. Using a catalyst consisting of a crystalline aluminosilicate faujasite Y-type zeolite which has been treated with a fluorosulfonic acid;b. continuously contacting said t-butanol and methanol in a molar amount of about 0.1 to 10 moles of methanol per mole of t-butanol with said catalyst at a temperature of about 20.degree. C. to about 250.degree. C. and a pressure of about atmospheric to about 1000 psig to obtain the methyl tert-butyl ether product.Type: GrantFiled: March 4, 1991Date of Patent: January 14, 1992Assignee: Texaco Chemical CompanyInventor: John F. Knifton
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Patent number: 5059725Abstract: Disclosed is a method wherein t-butanol is reacted with methanol in one step to provide methyl t-butyl ether at a temperature of about 20.degree. C. to 250.degree. C. and a pressure of about atmospheric to about 1000 psig employing a catalyst consisting of a Group IV oxide on which there has been deposited a sulfur-containing compound from the group consisting of ammonium sulfate or sulfuric acid.Type: GrantFiled: March 29, 1991Date of Patent: October 22, 1991Assignee: Texaco Chemical CompanyInventors: John F. Knifton, John R. Sanderson
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Patent number: 5047070Abstract: Alcohol feedstock containing water is extracted with olefinic liquid and reacted catalytically to produce tertiary ether. Unreacted alcohol and olefin vapor separated from etherification effluent is converted along with aqueous alcoholic raffinate in a zeolite catalysis step to produce gasoline and paraffinic intermediate. By dehydrogating the C.sub.3 -C.sub.5 paraffins, an olefinic liquid rich in isoalkenes is obtained for recycle to the extractor as solvent for alcohol feedstock.Type: GrantFiled: May 30, 1989Date of Patent: September 10, 1991Assignee: Mobil Oil CorporationInventors: Mohsen N. Harandi, Hartley Owen
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Patent number: 5041690Abstract: Methanol or other alcohol is converted to high octane gasoline components by an integrated process wherein crude aqueous alcohol feedstock is extracted with a liquid extractant stream containing C.sub.4 +iso-olefin and reacted to form tertiary-alkyl ethers, such as MTBE. The aqueous raffinate is converted to olefinic hydrocarbons in a MTO catalytic reactor. Propene from the MTO reaction is reacted with water to produce di-isopropyl ether, which may be blended with MTBE and C.sub.6 +MTO hydrocarbons to produce high octane gasoline. Isobutylene and isoamylenes from the MTO reaction can be recovered and recycled as a liquid extractant stream.Type: GrantFiled: August 3, 1990Date of Patent: August 20, 1991Assignee: Mobil Oil CorporationInventors: Mohsen N. Harandi, Hartley Owen
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Patent number: 5037511Abstract: A process for the production of pure dimethylether by feeding the dehydration product from a dimethylether-synthesis reactor into a distillation column for the production of pure dimethylether at defined trays of this column and withdrawal of pure dimethylether and a fraction containing contaminations at defined trays of the same column, whereby in addition washing liquids and bases can be added.Type: GrantFiled: April 28, 1989Date of Patent: August 6, 1991Inventors: Horst Dornhagen, Hartmut Hammer, Ewald Meisenburg, Horst Schmid
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Patent number: 5001292Abstract: An integrated process is disclosed that substantially reduces the cost of producing MTBE and other alkyl tert-alkyl ethers by eliminating a major portion of the equipment and operating costs associated with the downstream processing of the etherification reactor effluent. The integrated process combines the process for the etherification of isoolefins and methanol, or other alkanols, to produce methyl tertiary alkyl ethers such as MTBE and/or TAME with the catalytic process for converting feedstock such as oxygenates, light olefins and paraffins to higher molecular weight hydrocarbons. Unconverted reactants from the etherification reaction, which may comprise unreacted alkanol and unreacted hydrocarbons or just unreacted hydrocarbons, are separated from the product ethers and passed to the catalytic conversion process reactor for conversion to gasoline boiling range hydrocarbons.Type: GrantFiled: October 16, 1989Date of Patent: March 19, 1991Assignee: Mobil Oil CorporationInventors: Mohsen N. Harandi, Hartley Owen
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Patent number: 4990697Abstract: A process for producing homoallyl alcohols of the general formula (I) ##STR1## in which either A.sup.1 or A.sup.3 represents a hydrogen atom, the other represents a single bonding along with A.sup.2 ; R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different and independently represents a hydrogen atom, or an alkyl or alkenyl group with or without being substituted with a hydroxyl group or an akoxyl group; and Y represents a hydrogen atom, an alkyl group or an alkenyl group, by reacting 1,3-glycols of the general formula (II) ##STR2## in which X and Y are the same or different and independently represents a hydrogen atom, an alkyl group or an alkenyl group, R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 independently represents as defined above, at a temperature in the range of 130.degree. to 250.degree. C. in liquid phase with the contact of .gamma.-alumina catalyst.Type: GrantFiled: October 16, 1989Date of Patent: February 5, 1991Assignee: Kuraray Co., Ltd.Inventors: Tsumoru Renge, Osamu Yamada, Katumi Omura
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Patent number: 4935552Abstract: Light olefins are catalytically converted to ethers, e.g., propylene is converted to diisopropyl ether, in a dual stage process in which product ether is recycled to a first stage reaction zone to significantly reduce the operating temperature of the olefin hydration/etherification reactions taking place in that zone. Alcohol produced in the first stage reaction zone undergoes conversion in the second stage reaction zone, e.g., by etherification with light olefin or by catalytic distillation, to provide additional product ether. The process contemplates the use of zeolites as olefin hydration/etherification catalysts.Type: GrantFiled: January 12, 1989Date of Patent: June 19, 1990Assignee: Mobil Oil CorporationInventors: Jonathan E. Child, Byung C. Choi, Francis P. Ragonese
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Patent number: 4927977Abstract: A process and apparatus are provided for the substantially uniform distribution of a two-phase feed in a chemical reaction zone. As applied, for example, to the hydration/etherification of light olefin to alcohol(s) and/or ether(s), the invention results in greater process control and in particular cases, to improved reaction product selectivities.Type: GrantFiled: January 12, 1989Date of Patent: May 22, 1990Assignee: Mobil Oil CorporationInventors: Jonathan E. Child, Byung C. Choi, Francis P. Ragonese
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Patent number: 4925989Abstract: A process for preparing methyl tertiary-butyl ether wherein tertiary-butyl alcohol, isobutylene and methanol are continuously fed into a combination reactor distillation tower having a packed sulfonic acid resin catalyst beds where a substantially pure product of MTBE methyl tertiary-butyl ether is produced.Type: GrantFiled: June 1, 1987Date of Patent: May 15, 1990Assignee: Texaco Inc.Inventors: John J. Hagan, Sheldon Herbstman
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Patent number: 4918244Abstract: A process for preparing MTBE wherein TBA and MeOH are continuously fed to a rectification tower having a packed solid-acid catalyst bed where the TBA and MeOH react in the presence of the catalyst to produce MTBE.Type: GrantFiled: May 4, 1987Date of Patent: April 17, 1990Assignee: Texaco Inc.Inventors: Edward C. Nelson, David A. Storm, Mahendra S. Patel
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Patent number: 4886918Abstract: Light olefin is introduced at multiple points of entry into a conversion unit subdivided into first and second reaction zones. Reaction of olefin with water takes place in the first reaction zone under conditions intended to promote the production of alcohol therein and in the second reaction zone, alcohol produced in the first reaction zone is both dehydrated and reacted with olefin under conditions intended to promote the production of ether therein. The same or different shape selective acidic zeolites are employed as catalysts in both reaction zones.Type: GrantFiled: May 3, 1989Date of Patent: December 12, 1989Assignee: Mobil Oil CorporationInventors: Charles M. Sorensen, Philip Varghese
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Patent number: 4885405Abstract: This invention relates to a process for the production of pure dimethylether by catalytic dehydration of methanol in the presence of a .gamma.-Al.sub.2 O.sub.3 -catalyst which contains a small quantity of SiO.sub.2.Type: GrantFiled: December 10, 1987Date of Patent: December 5, 1989Inventors: Horst Dornhagen, Hartmut Hammer, Bernd Haas, Ewald Meisenburg
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Patent number: 4857664Abstract: Olefin undergoes conversion in the presence of water to a mixture of alcohol and ether which is then subjected to various downstream operations including distillation and decantation to provide an ether-rich product containing little if any water. If desired the ether can be combined in any predetermined ratio with co-produced alcohol to provide alcohol/ether mixtures of desired composition. The foregoing process is especially suitable to the conversion of propylene and propylene-containing streams to diisopropyl ether and mixtures of isopropyl alcohol and diisopropyl ether which are useful, inter alia, as octane improves for gasoline.Type: GrantFiled: October 27, 1988Date of Patent: August 15, 1989Assignee: Mobil Oil CorporationInventors: Tracy J. Huang, Rene B. LaPierre, Samuel A. Tabak
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Patent number: 4827048Abstract: A method is disclosed for producing methyl tertiary butyl ether by reacting tertiary butyl alcohol and methanol in the presence of a catalyst comprising a heteropoly acid, such as 12-tungstophosphoric acid or 12-molybdophosphoric acid, on an inert support, such as titania, at an elevated temperature and moderate pressure.Type: GrantFiled: March 14, 1988Date of Patent: May 2, 1989Assignee: Texaco Chemical CompanyInventor: John F. Knifton