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: 6486362Abstract: A process for producing oxygen-containing compounds containing at least one oxygen atom bonded to two distinct carbon atoms which are not bonded together and not comprising a multiple bond comprises a step a) for hydroformylation of a feed comprising at least one olefin containing four to seven carbon atoms to at least one aldehyde, in the presence of a catalyst and a synthesis gas under hydroformylation conditions, a step b) for hydrogenation of this aldehyde to at least one corresponding alcohol, and a step c) for transforming at least one alcohol obtained from step b) in the presence of a catalyst under conditions for producing a mixture containing at least one ether or at least one acetal.Type: GrantFiled: June 29, 2000Date of Patent: November 26, 2002Assignee: Institut Francais du PetroleInventors: Alain Forestiere, Jean-Ferdinand Gaillard, Michel Barraque
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Patent number: 6472569Abstract: A catalyst system comprising a silicoaluminophosphate impregnated with a compound selected from the group consisting of phosphoric acid, boric acid, tributyltin acetate, and combinations of any two or more thereof, and a method of preparing such catalyst system, are disclosed. The thus-obtained catalyst system is employed as a catalyst in the conversion of a hydrocarbon feedstock comprising oxygenated hydrocarbons to olefins and/or ethers.Type: GrantFiled: April 16, 1999Date of Patent: October 29, 2002Assignee: Phillips Petroleum CompanyInventors: An-hsiang Wu, Jianhua Yao, Charles A. Drake
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Patent number: 6458856Abstract: An improvement to the process for separating dimethyl ether (DME) from byproducts in a one-step catalytic conversion of synthesis gas (syngas), the improvement comprising using a scrubbing solvent comprising a mixture of dimethyl ether and methanol for the separation of dimethyl ether and carbon dioxide from the unconverted synthesis gas in a scrubbing column. Additional improvements include recycling of the scrubbing solution, multi-step processing of the liquid effluent from the scrubber, and methods of processing the methanol-water effluent of the flash column that is interposed between the DME reactor and the scrubber.Type: GrantFiled: November 7, 2001Date of Patent: October 1, 2002Assignee: Air Products and Chemicals, Inc.Inventors: Xiang-Dong Peng, Barry W. Diamond, Tsun-Chiu Robert Tsao, Bharat Lajjaram Bhatt
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Patent number: 6232508Abstract: A process for the manufacture of ether from a feedstock containing isoolefins and linear olefins. The process is one which has a high conversion of isoolefins thereby permitting the separation of linear olefins without the associated difficulty in separating isomers.Type: GrantFiled: February 12, 1996Date of Patent: May 15, 2001Assignee: Phillips Petroleum CompanyInventors: Gary R. Patton, Robert O. Dunn
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Patent number: 6218583Abstract: Process for the production of ethers starting from alcohols, in the presence of liquid acid catalysts, essentially comprising the following steps: a) sending a stream containing C4-C10 alcohols to a reaction zone obtaining a product essentially consisting of ethers and the acid catalyst; b) feeding the product essentially consisting of ethers and the acid catalyst to an extraction zone with C4-C10 alcohols in order to obtain a stream essentially consisting of ethers and a stream containing said alcohols and said catalyst; c) sending the non-reacted alcohols and the water formed by the reaction zone to a distillation zone from which an azeotropic alcohol/water stream is obtained together with the residual stream which is sent to the reaction zone; d) sending the azeotropic alcohol/water stream to a separation zone to separate the alcohol, which is recycled to the reaction zone, from the aqueous stream.Type: GrantFiled: March 23, 1998Date of Patent: April 17, 2001Assignee: Snamprogetti S.p.A.Inventors: Renata Patrini, Mario Marchionna
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Patent number: 6218582Abstract: 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 comprising unreacted methanol, unreacted tertiary butyl alcohol, water, isobutylene and methyl tertiary butyl ether, that is separated into a substantially anhydrous 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, and wherein the isobutylene and methanol in the first distillation fraction are reacted to form an isobutylene conversion product that contains additional methyl tertiary butyl ether that is substantially free from tertiary butyl alcohol.Type: GrantFiled: May 19, 1995Date of Patent: April 17, 2001Assignee: Huntsman International LLCInventors: Charles Joseph Kruse, Kyle Lee Preston, Brian Lawrence Benac
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Patent number: 6133484Abstract: A tertiary butyl alcohol charge stock typically contaminated with from about 0.5 to about 2 wt. % of formates and peroxides, is passed through an oxygenates decomposition reactor containing a bed of a decomposition catalyst comprising rhodium, platinum, palladium or mixture thereof at a temperature of from about 100 to about 280C to decompose the peroxides and formates, and to dehydrate a portion of the tertiary butyl alcohol to form isobutylene and water to thereby form a non-corrosive tertiary butyl alcohol feedstock that is substantially free from formates that is suitable for reaction with methanol in a methyl tertiary butyl ether etherification reactor to form a non-corrosive methyl tertiary butyl ether etherification reaction product from which methyl tertiary butyl ether can be recovered.Type: GrantFiled: February 18, 1999Date of Patent: October 17, 2000Assignee: Huntsman ICI Chemical LLCInventors: John Frederick Knifton, John Ronald Sanderson, William Alan Smith, James Douglas Goshinska, Mark Allen Mueller
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Patent number: 6090988Abstract: A reaction mixture in a gas form which is obtained by intramolecular dehydration of glycol ether in a gas phase is liquidized and collected by using as a collecting agent the glycol ether which is a raw material of the reaction mixture. The collected liquid thus obtained is continuously distilled by using a continuous distillation column so that a distillate containing alkyl vinyl ether and water is obtained, while a bottom product containing glycol ether is obtained. The distillate is left to stand in a separation vessel whereby separating into an oleaginous layer and an aqueous layer, so that alkyl vinyl ether is collected as the oleaginous layer. On the other hand, in the case where the bottom product contains water, the bottom product is continuously distilled together with an azeotrope former by using a continuous distillation column whereby a distillate containing an azeotrope of water and the azeotrope former, so that glycol ether is collected as a bottom product.Type: GrantFiled: March 18, 1998Date of Patent: July 18, 2000Assignee: Nippon Shokubai Co., Ltd.Inventors: Hideyuki Kambe, Hitoshi Yano, Yuuji Shimasaki
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Patent number: 6063966Abstract: An impure methyl tertiary butyl ether product contaminated with isobutylene, methanol and water is purified by continuous counter-current contact with water and an isobutylene fraction in an extraction zone comprising a counter-current contact tower to provide an overhead raffinate comprising isobutylene, methyl tertiary butyl ether and a minor amount of water and an extract 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 returned to the contact tower as the isobutylene fraction.Type: GrantFiled: September 1, 1994Date of Patent: May 16, 2000Assignee: Huntsman ICI Chemicals LLCInventors: Michael Warren Peters, Yu-Hwa Edward Sheu
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Patent number: 5985100Abstract: Butanol and dibutyl ether are separated from a mixture containing water, dibutyl ether and n-butanol, 2-butanol and/or isobutanol by a process in whicha) the mixture is introduced into a first distillation column, essentially butanol is separated off at the bottom of this distillation column and the mixture taken off at the top of the distillation columnb) is introduced into a second distillation column and essentially dibutyl ether is separated off at the bottom of this second distillation column and the mixture formed at the top of the second distillation column is removed,c) the second distillation column being operated at a higher pressure than the first distillation column and at least one of the two mixtures taken off via the top of the distillation columns being subjected to phase separation, only the organic phase separated off being fed to the second distillation column in the case of phase separation downstream of the first distillation column, and separation into an aqueous and an organic phase alsType: GrantFiled: February 17, 1998Date of Patent: November 16, 1999Assignee: BASF AktiengesellschaftInventors: Maik Aron, Harald Rust
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Patent number: 5962750Abstract: A process for treating a feedstock containing olefins of 6 carbon atoms per molecule, said olefins being either potentially etherifiable or (directly) etherifiable, wherein isomerization of a portion of the potentially etherifiable olefins is accomplished in part in an isomerization zone, in the presence of an isomerization catalyst that makes it possible to obtain an isomerization effluent which comprises in part etherifiable olefins, and in that, in part, etherification is carried out, in the presence of an etherification catalyst and at least one alcohol that has 1 to 4 carbon atoms per molecule, of a portion of etherifiable olefins that are contained in the feedstock, in a first etherification zone, and in part etherification is carried out of a portion of etherifiable olefins that are contained in said isomerization effluent, in a second etherification zone, in the presence of an etherification catalyst and at least one alcohol that has 1 to 4 carbon atoms per molecule, to optimize the production of etheType: GrantFiled: February 15, 1996Date of Patent: October 5, 1999Assignee: Institut Francais Du PetroleInventors: Charles Cameron, Alain Forestiere, Marie-Claire Marion, Jean-Luc Nocca, Jean-Luc Duplan
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Patent number: 5919989Abstract: The overheads from an etherification distillation column reactor containing unreacted alcohol and isoolefin are fed to a finishing reactor and then a portion of the effluent from the finishing reactor is returned to the distillation column reactor.Type: GrantFiled: June 20, 1997Date of Patent: July 6, 1999Assignee: Catalytic Distillation TechnologiesInventors: Amarjit Bakshi, Thomas P. Hickey
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Patent number: 5908963Abstract: A process for the preparation of dimethyl ether. The process prepares fuel grade dimethyl ether from a hydrogen and carbon oxides synthesis gas.Type: GrantFiled: December 12, 1997Date of Patent: June 1, 1999Assignee: Holdor Topsoe A/SInventors: Bodil Voss, Finn Joensen, John Bogild Hansen
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Patent number: 5856588Abstract: Methyl tertiary butyl ether is prepared from tertiary butyl alcohol and methanol in a plural stage process by (a) reacting tertiary butyl alcohol with methanol in a primary MTBE reaction zone containing a cationic ion-exchange resin catalyst to form a primary reaction product, (b) fractionating the primary reaction product in a primary distillation zone to provide a first lighter, lower boiling distillation fraction comprising isobutylene, methanol and methyl tertiary butyl ether and a first heavier, higher boiling distillation fraction comprising methanol, tertiary butyl alcohol and water, c) contacting the first heavier distillation fraction in a second stage reactor containing a second stage acidic, fluoride-treated Y-zeolite having a silica:alumina ratio of 100:1 to 10:1 and a unit cell size of from 24.20 to 24.45 .ANG. or a fluoride-treated silicoaluminophosphate (SAPO) molecular sieve having a pore size of from 5 .ANG. to 8 .ANG., under conversion conditions including a temperature of from 20.degree.Type: GrantFiled: December 30, 1996Date of Patent: January 5, 1999Assignee: Huntsman Specialty Chemicals CorporationInventors: Pei-Shing Eugene Dai, John Frederick Knifton
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Patent number: 5831116Abstract: A process for partially oxidizing alcohols such as methanol, comprising the steps of a) introducing into a reactor unit containing a solid acid catalyst amounts of alcohol and oxygen; and a supercritical fluid (such as SCF CO.sub.2) mobile phase; and b) partially oxidizing the alcohol to its corresponding ether, aldehyde, ester or acid. In an advantageous embodiment, methanol is oxidized using an aerogel acid catalyst to produce methyl ether.Type: GrantFiled: April 18, 1997Date of Patent: November 3, 1998Assignee: Northeastern UniversityInventors: Chien-Tsung Wang, Ronald J. Willey
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Patent number: 5817906Abstract: The present invention relates to a process for the production of light olefins comprising olefins having from 2 to 4 carbon atoms per molecule from a crude oxygenate feedstock. The crude oxygenate feedstock comprises an alcohol, and water. The process comprises passing the crude oxygenate feedstock to catalyst to a distillation with reaction zone to convert the alcohol to an ether and produce an ether product having a reduced water relative to the crude oxygenate feedstock and a first water stream. The ether product is passed to an oxygenate conversion zone containing a metal aluminosilicate catalyst to produce a light olefin stream.Type: GrantFiled: August 10, 1995Date of Patent: October 6, 1998Assignee: UOP LLCInventors: Terry L. Marker, Christopher David Gosling
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Patent number: 5811597Abstract: Methyl tertiary butyl ether is prepared from contaminated TBA by reactively distilling the contaminated TBA in a reactive distillation column to provide a lower boiling isobutylene fraction and a higher boiling aqueous TBA fraction, by distilling the higher boiling aqueous TBA fraction to provide a lower boiling TBA fraction, by charging the lower boiling isobutylene fraction, the lower boiling tertiary butyl alcohol fraction and methanol to an etherification reactor to form an etherification reaction product, by distilling the etherification reaction product to provide a lower boiling fraction containing isobutylene, methanol and methyl tertiary butyl ether by charging the lower boiling fraction to a finishing reactor to react the isobutylene and methanol contained therein to from additional MTBE and by recovering MTBE from the etherification reaction product and the isobutylene conversion product.Type: GrantFiled: August 26, 1996Date of Patent: September 22, 1998Assignee: Huntsman Specialty Chemicals Corp.Inventors: Rei-Yu Judy Hwan, Mark Elliott Taylor, John Frederick Knifton, Melvin Ernest Stockton, John Ronald Sanderson
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Patent number: 5792890Abstract: A tertiary butyl alcohol charge stock contaminated with from about 0.5 to about 2 wt. % of corrosive oxygen-containing impurities, including peroxides and formates, is passed through an oxygenates decomposition reactor containing a bed of a basic zeolite catalyst to decompose the peroxides and oxygen-containing impurities, including peroxides and formates, and to dehydrate a portion of the tertiary butyl alcohol to form isobutylene and water to form a substantially less-corrosive tertiary butyl alcohol feedstock that is substantially free from oxygen-containing impurities, including formates that is suitable for reaction with methanol in a methyl tertiary butyl ether etherification reactor to form a methyl tertiary butyl ether etherification reaction product from which methyl tertiary butyl ether can be recovered.Type: GrantFiled: February 3, 1997Date of Patent: August 11, 1998Assignee: Huntsman Specialty Chemicals Corp.Inventors: Pei-Shing Eugene Dai, Laurence Darrel Neff, Kyle Lee Preston, Rei-Yu Judy Hwan, John Frederick Knifton
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Patent number: 5789627Abstract: Methyl tertiary butyl ether is prepared from contaminated tertiary butyl alcohol and methanol by decomposing peroxides in a peroxides decomposition reactor, by dehydrating the tertiary butyl alcohol to form isobutylene and also decomposing acidic contaminants in a tertiary butyl alcohol dehydration reactor to form a feedstock that is distilled to provide a first lower boiling fraction comprising isobutylene and water; from which isobutylene is recovered for reaction with methanol in an etherification reactor containing a bed of an etherification catalyst to form methyl tertiary butyl ether.Type: GrantFiled: February 20, 1997Date of Patent: August 4, 1998Assignee: Huntsman Specialty Chemicals Corp.Inventors: Rei-Yu Judy Hwan, Kyle Lee Preston
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Patent number: 5780689Abstract: In accordance with the present invention, there is now provided a novel selective catalyst useful for the synthesis of methyl-tert-butyl ether (MTBE) or ethyl-tert-butyl ether (ETBE) prepared by reacting isobutene with methanol or ethanol, respectively. More specifically, the catalyst of the present invention comprises from about 0.5 to about 7% by weight of triflic acid (trifluoro-methanesulfonic acid, CF.sub.3 SO.sub.3 H, hereafter referred to as TFA) incorporated onto an acid form Y zeolite.Type: GrantFiled: August 30, 1995Date of Patent: July 14, 1998Assignee: Societe Quebecoise D'Initiatives PetrolieresInventor: Raymond Le Van Mao
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Patent number: 5773669Abstract: There is provided a simple and rational process for production of a vinyl ether, which comprises subjecting a 2-hydroxyalkoxy compound having, in the molecule, at least one 2-hydroxyalkoxy group and at least one functional group selected from the group consisting of a hydroxyl group and an amino group, to an intramolecular dehydration reaction in a gas phase to convert the compound into a corresponding functional group-containing vinyl ether in one step without using any subsidiary raw material or any solvent. The process is characterized by using, as a catalyst, an oxide containing an alkali metal element and/or an alkaline earth metal element and silicon.Type: GrantFiled: March 11, 1997Date of Patent: June 30, 1998Assignee: Nippon Shokubai Co., Ltd.Inventors: Yuuji Shimasaki, Akira Kurusu
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Patent number: 5763712Abstract: This invention relates to a process for the preparation and fractionation of a mixture of dimethyl ether and chloromethane by extractive distillation with methanol as extractant. The mixture is prepared by reacting methanol with hydrogen chloride. The mixture is then distilled to remove water and is subsequently subjected to an extractive distillation with methanol as extractant, with chloromethane resulting as top product. In another distillation step, the remaining dimethyl ether is separated from the methanol.Type: GrantFiled: June 23, 1997Date of Patent: June 9, 1998Assignee: Hoechst AktiengesellschaftInventors: Peter Roth, Erhard Leistner, Wolfgang Wendel
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Patent number: 5763685Abstract: MTBE is prepared from TBA and MeOH by passing a feed mixture comprising TBA and MeOH through a primary MTBE reaction zone to form a primary reaction product containing MTBE, unreacted TBA, unreacted MeOH, isobutylene and water; the primary reaction product is fractionated to provide a first lighter distillation fraction comprising isobutylene, MeOH and MTBE and a first higher boiling distillation fraction comprising MeOH, TBA and water and the first higher boiling distillation fraction is charged to a second stage MTBE reaction zone to form a second stage reaction product comprising unreacted MeOH, unreacted TBA water, isobutylene and MTBE.Type: GrantFiled: August 17, 1995Date of Patent: June 9, 1998Assignee: Huntsman Specialty Chemicals CorporationInventors: Charles Joseph Kruse, Kyle Lee Preston, Brian Lawrence Benac
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Patent number: 5750799Abstract: A process for production and recovery of dimethyl ether by dehydration of methanol which significantly reduces the distillation duties associated to the preparation of the fresh methanol feed stock and/or the recovery of unconverted methanol for use as recycle feed stock to the dimethyl ether production process while maintaining a high rate of conversion of methanol to dimethyl ether.Type: GrantFiled: March 15, 1995Date of Patent: May 12, 1998Assignee: Starchem, Inc.Inventor: Christiaan P. van Dijk
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Patent number: 5744652Abstract: Methyl tertiary butyl ether is prepared from TBA contaminated with oxygen-containing impurities by decomposing the impurities to gaseous products, by charging the thus-treated tertiary butyl alcohol and methanol to an etherification reactor to form an etherification reaction product, by distilling the etherification reaction product to provide a lower boiling fraction containing isobutylene, methanol and methyl tertiary butyl ether by charging the lower boiling fraction to a finishing reactor to react the isobutylene and methanol contained therein to from additional MTBE and by recovering MTBE from the etherification reaction product and the isobutylene conversion product.Type: GrantFiled: March 10, 1997Date of Patent: April 28, 1998Assignee: Huntsman Specialty Chemicals Corp.Inventors: Pei-Shing Eugene Dai, Laurence Darrel Neff, Kyle Lee Preston, Rei-Yu Judy Hwan
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Patent number: 5741952Abstract: An MTBE recycle stream (which consists mainly of TBA and methanol) contaminated with residual amounts of tertiary butyl hydroperoxide, ditertiary butyl peroxide and allyl tertiary butyl peroxide can be effectively catalytically treated under mild conversion conditions with a silica-supported nickel, copper, chromium, iron catalyst in order to substantially completely decompose the peroxide contaminants and to thereby provide a treated MTBE recycle stream which is not only substantially free from contaminating quantities of such peroxides, but which also contains an enhanced amount of methyl tertiary butyl ether.Type: GrantFiled: January 11, 1993Date of Patent: April 21, 1998Assignee: Huntsman Specialty Chemicals CorporationInventors: John Ronald Sanderson, John Frederick Knifton
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Patent number: 5741953Abstract: An aqueous methanol feed stream contaminated with tertiary butyl alcohol is charged to a reactive distillation column having a reaction distillation section in the upper portion thereof containing an acid cation exchange resin and separated therein into a substantially anhydrous lower boiling methanol fraction contaminated with isobutylene and a higher boiling water fraction by charging the feed stream to the lower portion of the reactive distillation column to separate the feed stream into a higher boiling water fraction and a lower boiling methanol fraction containing a tertiary butyl alcohol-water azeotrope for upward flow into the reactive distillation section for reaction of the tertiary butyl alcohol to form isobutylene, MTBE and water and recovery of a substantially anhydrous lower boiling methanol fraction contaminated with isobutylene and MTBE.Type: GrantFiled: August 17, 1995Date of Patent: April 21, 1998Assignee: Huntsman Specialty Chemicals CorporationInventor: Kyle Lee Preston
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Patent number: 5741951Abstract: Methyl tertiary butyl ether and diisobutylene are prepared by reacting methanol with tertiary butyl alcohol to provide an etherification reaction product containing methyl tertiary butyl ether, tertiary butyl alcohol, methanol, isobutylene, and water. A methyl tertiary butyl ether product fraction and an isobutylene fraction are recovered from the etherification reaction product; the isobutylene fraction is charged to an isobutylene conversion reaction zone to form a diisobutylene conversion product, and the diisobutylene conversion product is charged to a diisobutylene distillation zone and separated therein into a lower boiling distillation fraction comprising isobutylene, and diisobutylene and a higher boiling distillation fraction consisting essentially of diisobutylene.Type: GrantFiled: December 30, 1996Date of Patent: April 21, 1998Assignee: Huntsman Specialty Chemicals CorporationInventor: Kyle Lee Preston
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Patent number: 5721305Abstract: Glycerol, 2,2-dimethyl-1,3-dioxolane-4-methanol (Solketal), glycidol or glycerol carbonate is polymerized into preponderantly linear oligomers at 150.degree. C. to 350.degree. C. in the presence of anionic clay material, preferably hydrotalcite, as a catalyst.Type: GrantFiled: June 12, 1996Date of Patent: February 24, 1998Assignee: Unichema Chemie B.V.Inventors: Johan Jan W. Eshuis, Johannes Arie M. Laan, Glyn Roberts
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Patent number: 5705712Abstract: A highly integrated process for concurrently producing diisopropyl ether and an isopropyl tertiary alkyl ether has been developed. Optionally, high purity isopropyl alcohol may also be collected as a product. In a first reactor, propylene and water are reacted to form isopropyl alcohol, a portion of which is further reacted to form diisopropyl ether. After removing unreacted propylene, the effluent of the first reactor is separated into an ether rich stream, a water rich stream and an alcohol rich stream. The alcohol rich stream is dried to provide dry isopropyl alcohol. A portion of the dry isopropyl alcohol may be removed and collected as a product. A portion of the dry isopropyl alcohol and isobutylene, isoamylene or a mixture thereof are reacted to form an isopropyl tertiary alkyl ether in a second reactor. Unreacted iso-olefins and inert compounds are then removed from the second reactor effluent.Type: GrantFiled: October 5, 1995Date of Patent: January 6, 1998Assignee: UOPInventors: Stanley J. Frey, Robert J. Schmidt, Terry L. Marker, Richard E. Marinangeli
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Patent number: 5705711Abstract: Tertiary butyl alcohol and methanol are reacted in a primary reactor in the presence of an acid cation exchange resin to provide a primary reaction product comprising methyl tertiary butyl ether, unreacted tertiary butyl alcohol, unreacted methanol, isobutylene, water and oxygen-containing by-products, and the primary reaction product is charged to a reactive distillation column where additional methyl tertiary butyl ether is prepared from the methanol, tertiary butyl alcohol and isobutylene present in the primary reaction product.Type: GrantFiled: August 17, 1995Date of Patent: January 6, 1998Assignee: Huntsman Specialty Chemicals CorporationInventor: Kyle Lee Preston
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Patent number: 5689013Abstract: The present invention concerns a process for preparing tertiary alkyl ethers. The process comprises the steps of contacting in the presence of a catalyst a feedstock containing saturated hydrocarbons and dienes having 4 to 7 carbon atoms with an excess of hydrogen in relation to the amount of dienes in the feed in order selectively to hydrogenate at least a part of the dienes, feeding the treated hydrocarbon feedstock together with at least a part of the unreacted hydrogen to a catalytic distillation reactor system which includes at least one distillation column, reacting the C.sub.4-7 isoolefines of the feedstock with methanol or ethanol in the presence of a catalyst to form tertiary alkyl ethers, subjecting the reaction mixture to distillation in the distillation column, recovering the alkyl ethers and substantially all of the unreacted hydrocarbons with the bottoms product of the distillation, withdrawing an overhead product of the distillation, which mainly contains an azeotrope of saturated C.sub.Type: GrantFiled: September 12, 1995Date of Patent: November 18, 1997Assignee: Neste OtInventors: Harri Jarvelin, Petri Lindqvist, Juha Jakkula
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Patent number: 5689014Abstract: A highly integrated process for concurrently producing diisopropyl ether and an isopropyl tertiary alkyl ether has been developed. In a first reactor, propylene and water are reacted to form isopropyl alcohol, a portion of which is further reacted to form diisopropyl ether. After removing unreacted propylene, the effluent of the first reactor is separated into an ether rich stream, a water rich stream and an alcohol rich stream. The alcohol rich stream and isobutylene, isoamylene or a mixture thereof are reacted to form an isopropyl tertiary alkyl ether in a second reactor. The water present in the alcohol rich stream also reacts with the iso-olefin to form tertiary alcohol. The effluent from the second reactor is water washed to produce an oxygenate product stream and an aqueous alcohol recycle stream. Some tertiary alcohol is recycled to the first reactor where it is reacted with propylene to form additional isopropyl tertiary alkyl ether.Type: GrantFiled: October 5, 1995Date of Patent: November 18, 1997Assignee: UOPInventors: Stanley J. Frey, Robert J. Schmidt, Terry L. Marker, Richard E. Marinangeli
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Patent number: 5684213Abstract: A method for producing dialkyl ethers comprising feeding a stream containing a C.sub.1 to C.sub.4 alcohol to a distillation column reactor into a feed zone, contacting the stream with a fixed bed zeolite prepared as a distillation structure to form the corresponding dialkyl ether and water, and concurrently fractionating the ether product from the water and unreacted materials wherein the improvement is the addition of a small amount of hydrogen to the reaction zone to inhibit catalyst fouling and substantially increasing the catalyst life and activity.Type: GrantFiled: March 25, 1996Date of Patent: November 4, 1997Assignee: Chemical Research & Licensing CompanyInventors: Speros Peter Nemphos, Dennis Hearn
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Patent number: 5663454Abstract: Methanol and isobutylene are reacted to form a methyl tertiary butyl ether product stream containing contaminating quantities of dimethyl ether, methanol and isobutylene that is separated into a first fraction comprising isobutylene and methyl tertiary butyl ether and a second fraction comprising residual methyl tertiary butyl ether, methanol, dimethyl ether and water. The second fraction is separated into a first lower boiling distillation fraction comprising methyl tertiary butyl ether, methanol, isobutylene, dimethyl ether, and water and a first higher boiling distillation fraction comprising methanol and water. Dimethyl ether and isobutylene are recovered from the first lower boiling distillation fraction and charged to a second distillation column for separation into a second lower boiling distillation fraction consisting essentially of dimethyl ether and a second higher boiling distillation fraction comprising dimethyl ether and isobutylene.Type: GrantFiled: August 8, 1995Date of Patent: September 2, 1997Assignee: Huntsman Specialty Chemicals CorporationInventor: Kyle Lee Preston
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Patent number: 5659090Abstract: The invention concerns steps in a process for the synthesis of at least one alkyl tertiobutyl ether, preferably respectively MTBE or ETBE, from at least one alcohol and from isobutene, each synthesized at least partially from natural gas. The alcohol, preferably methanol or ethanol respectively, is synthesized at least partially from synthesis gas, a portion of said synthesis gas being prepared in a natural gas steam prereforming zone. The isobutene is synthesized in a series of processes which includes direct transformation of natural gas to ethylene, known as oxidative coupling of methane (OCM), dimerisation of ethylene to normal butene, isomerisation of n-butene to isobutene, and the separation units associated therewith.Type: GrantFiled: October 19, 1995Date of Patent: August 19, 1997Assignees: Institut Francais Du Petrole, Elf Aquitaine ProductionInventors: Charles Cameron, Patrick Chaumette, Quang Dang Vu, Jacques Bousquet, Jacques Tournier-Lasserve, Guy Desgrandchamps
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Patent number: 5650544Abstract: The present invention provides a process for producing an unsaturated ether, which comprises subjecting a glycol ether to intramolecular dehydration in a gas phase in the presence of a catalyst to convert the glycol ether into an unsaturated ether directly in a one-step reaction. As the catalyst, an oxide containing, for example, silicon and an alkali metal is used. The process, which uses no auxiliary raw material, can produce an unsaturated ether (a vinyl ether and/or an allyl ether) simply and safely without generating any waste material derived from the auxiliary raw material.Type: GrantFiled: September 15, 1995Date of Patent: July 22, 1997Assignee: Nippon Shokubai Co., Ltd.Inventors: Kimio Ariyoshi, Yuuji Shimasaki
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Patent number: 5637778Abstract: Disclosed is a one-step method for synthesis of methyl tertiary butyl ether, diisopropyl ether and isopropyl ether from crude streams containing acetone, methanol and t-butyl alcohol which comprises reacting an acetone-rich feed over a bifunctional catalyst comprising 5-45% by weight of a catalyst consisting essentially of a hydrogenation catalyst selected from the group consisting of one or more metals selected from the group consisting of IB, VIB or VIII of the Periodic Table and a heteropoly acid on a 55%-95% of the total weight of the catalyst of a support comprising a compound selected from the group consisting of:a. a metal phosphate;b. 5 to 95% by weight metal phosphate supported on 95 to 5 wt % Group III or IV oxide; andc. a large pore silicoaluminophosphate.Type: GrantFiled: August 8, 1994Date of Patent: June 10, 1997Assignee: Texaco Chemical Inc.Inventors: Robert J. Taylor, Jr., Pei-Shing E. Dai, John F. Knifton, Bobby R. Martin
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Patent number: 5616679Abstract: A polyalkylene glycol having the general formula:HO--[R--O--].sub.n Hin which n has a value of at least 2 and R is an alkylene radical containing at least 20 carbon atoms is provided. Preferred polyalkylene glycols have an alkylene radical which is a branched alkylene radical containing at least 10 carbon atoms in the main chain and a degree of polymerization such that n is from 4 to 7. The polyalkylene glycol is prepared by the acid-catalyzed polycondensation of a monomeric alkylene glycol at elevated temperature.Type: GrantFiled: November 14, 1995Date of Patent: April 1, 1997Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Matthias Fies, Roland Gr utzmacher, Alfred Westfechtel
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Patent number: 5616814Abstract: An improved method of recovering methyl tertiary butyl ether from an etherification reaction product containing acidic by-products wherein the reaction product is charged to an MTBE distillation zone and fractionated therein to provide a lower boiling distillation fraction comprising isobutylene, methyl tertiary butyl ether, methanol and acidic by-products, wherein the lower boiling distillation fraction is counter-currently washed with alkaline water in a methanol extraction tower, and wherein an aqueous solution of an alkali is injected into the tower below the charge point for the wash water to substantially completely neutralize the acidic by-products and to provide an overhead extract substantially free from acidic by-products comprising isobutylene, methyl tertiary butyl ether and a minor amount of water, and a bottoms raffinate comprising methanol, water, alkaline by-products and a minor amount of methyl tertiary butyl ether.Type: GrantFiled: August 17, 1995Date of Patent: April 1, 1997Assignee: Texaco Chemical Inc.Inventor: Kyle L. Preston
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Patent number: 5600024Abstract: A process for producing ethyl tertiary butyl ether and for the substantially complete recovery by fractional distillation of the unreacted ethanol contained in an etherification reaction zone product stream as a product along with the ethyl tertiary butyl ether reaction product. This process utilizes methanol as a fractionator feed additive to enhance the recovery of ethanol as a bottoms product.Type: GrantFiled: July 26, 1995Date of Patent: February 4, 1997Assignee: Phillips Petroleum CompanyInventors: Robert B. Eldridge, Gary R. Patton
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Patent number: 5583266Abstract: A two-step integrated process for the generation of diisopropyl ether from a crude by-product acetone stream which comprises:a) Hydrogenating said crude acetone over a supported, hydrogenation catalyst to give an isopropanol-rich effluent;b) passing said isopropanol-rich intermediate directly to a second reactor, andc) subject said IPA to dehydration conditions in the presence of hydrogen and a strong acid zeolite catalyst from the group consisting of .beta.-zeolite, optionally modified with one or more metals from Groups IB, VIB, VIIB and VIII of the Periodic Table, and a dealuminized Y-zeolite.Type: GrantFiled: May 2, 1994Date of Patent: December 10, 1996Assignee: Texaco Inc.Inventors: Robert J. Taylor, Jr., Pei-Shing E. Dai, John F. Knifton
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Patent number: 5576464Abstract: MTBE, prepared by reacting MeOH with TBA to form a primary etherification reaction product, is distilled in a first distillation column to provide a first lower boiling distillation fraction comprising methyl tertiary butyl ether, isobutylene, methanol, dimethyl ether, and the first lower boiling fraction is water washed to provide an overhead extract that is distilled in a second distillation column to provide a second lower boiling distillation fraction comprising isobutylene, dimethyl ether and water, which is dewatered to provide a feed fraction comprising isobutylene and dimethyl ether that is reacted with less than an equivalent amount of MeOH to provide a secondary reaction product comprising MTBE, less than 0.5 wt. % of MeOH, isobutylene and contaminants including TBA and dimethyl ether, and the secondary reaction product is recycled to the second distillation column.Type: GrantFiled: August 8, 1995Date of Patent: November 19, 1996Assignee: Texaco Chemical Inc.Inventor: Kyle L. Preston
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Patent number: 5563301Abstract: Methyl tertiary butyl ether is sequentially prepared from tertiary butyl alcohol and methanol by:passing tertiary butyl alcohol and methanol through a primary reaction zone to form a primary etherification reaction product comprising unreacted methanol, unreacted tertiary butyl alcohol, water, dimethyl ether, isobutylene and methyl tertiary butyl ether;separating the primary etherification reaction product into a methanol recycle fraction, a tertiary butyl alcohol recycle fraction, an isobutylene fraction and a methyl tertiary butyl ether product fraction;recycling the methanol recycle fraction and the tertiary butyl alcohol recycle fraction to the methyl tertiary butyl ether etherification reaction zone;passing at least a portion of said isobutylene fraction together with added methanol through a secondary reaction zone to form a secondary etherification reaction product comprising water, methanol, isobutylene, DME, methyl tertiary butyl ether and tertiary butyl alcohol; andrecovering the methyl tertiary butType: GrantFiled: November 28, 1994Date of Patent: October 8, 1996Assignee: Texaco Development Corp.Inventors: Kyle L. Preston, Lawrence E. Tillotson, Rei-Yu J. Hwan
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Patent number: 5550300Abstract: Disclosed is an integrated process for the generation of a mixture of ethers, such as diisopropyl ether, methyl tertiary butyl ether, and/or isopropyl tertiary butyl ether, from a crude by-product acetone stream composed of acetone, tertiary butyl alcohol and methanol by passing such a stream, in the presence of hydrogen, over a catalyst system characterized by having both a hydrogenation activity gradient along the reactor in one direction and an etherification activity gradient in the opposite direction.Type: GrantFiled: December 30, 1994Date of Patent: August 27, 1996Assignee: Texaco Chemical Inc.Inventors: Robert J. Taylor, Jr., Pei-Shing E. Dai, John F. Knifton
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Patent number: 5527970Abstract: Disclosed is an improved process for preparing ethyl t-butyl ether in one-step which comprises reacting tertiary butanol and ethanol in the presence of a catalyst consisting essentially of a macroreticular acid resin or a pentasil zeolite at a temperature of about 40.degree.-140.degree. C. and atmospheric pressure to about 500 psig.Type: GrantFiled: February 2, 1995Date of Patent: June 18, 1996Assignee: Texaco Chemical Inc.Inventors: Rei-Yu J. Hwan, John F. Knifton, Brian L. Benac
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Patent number: 5476972Abstract: Disclosed is a one-step method for synthesis of ethers from mixtures of acetone and t-butyl alcohol which comprises reacting an acetone-rich feed over a bifunctional catalyst comprising 5%-45% by weight hydrogenation catalyst on 55%-95% of the total catalyst weight of a support comprising a zeolite and a Group III or IV oxide.Type: GrantFiled: January 28, 1994Date of Patent: December 19, 1995Assignee: Texaco Chemical Inc.Inventors: Pei-Shing E. Dai, Robert J. Taylor, Jr., John F. Knifton, Bobby R. Martin
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Patent number: 5449838Abstract: Disclosed is a two-step process for the generation of isopropyl t-butyl 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) subjecting said isopropanol-rich intermediate to etherification conditions in the presence of a strong acid catalyst selected from:(1) a cationic resin;(2) a .beta.-zeolite;(3) dealuminized Y-zeolites; and(4) metal-modified .beta.-zeolites.Type: GrantFiled: December 30, 1993Date of Patent: September 12, 1995Assignee: Texaco Chemical Inc.Inventors: John F. Knifton, Ernest L. Yeakey, Pei-Shing E. Dai
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Patent number: 5449839Abstract: Disclosed is an improved process for preparing ethyl t-butyl ether in one step which comprises reacting tertiary butanol and ethanol in the presence of a catalyst selected from zeolite beta and zeolite beta modified with multimetals 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 140.degree. C., the product comprises a two-phase mix of an ETBE-isobutylene and, optionally, diisobutylene product-rich phase and a heavier aqueous ethanol-rich phase.Type: GrantFiled: July 22, 1994Date of Patent: September 12, 1995Assignee: Texaco Chemical Inc.Inventors: John F. Knifton, Pei-Shing E. Dai
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Patent number: 5446210Abstract: A process for the production of polyol ethers comprising the steps ofA) reacting a mixture of at least one polyol and at least one carbonyl compound of the formulaR.sup.1 --CO--R.sup.2 (I)in which R.sup.1 and R.sup.2 independently of one another represent hydrogen or aliphatic hydrocarbon radicals containing 1 to 22 carbon atoms and 0, 1, 2, or 3 double bonds, with hydrogen at an elevated temperature in the presence of a hydrogenation catalyst which is insoluble in the reaction mixture; andB) removing the polyol ether-containing reaction product from the catalyst.Type: GrantFiled: January 21, 1994Date of Patent: August 29, 1995Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Udo Hees, Georg Assman, Fritz Schuster