From Polyolefins Patents (Class 560/244)
-
Patent number: 11384045Abstract: A method for producing a 1,3-bisacyloxy-2-methylenepropane represented by the following general formula (II), including reacting a carboxylic acid represented by the following general formula (I), isobutylene, and oxygen, in a liquid phase, in the presence of a catalyst containing a carrier having carried thereon palladium and a transition metal of Group 11 in the periodic table, and a catalyst activator.Type: GrantFiled: July 24, 2019Date of Patent: July 12, 2022Assignee: KURARAY CO., LTD.Inventors: Naoya Minamoto, Yusuke Murata
-
Patent number: 8491758Abstract: A process for inhibiting polymerization of (meth)acrylic acid and/or (meth)acrylic esters by introducing an oxygenous gas into the (meth)acrylic acid and/or the (meth)acrylic ester, in which the (meth)acrylic acid and/or the (meth)acrylic ester has a degree of purity of at least 95% and is in the liquid state.Type: GrantFiled: December 9, 2010Date of Patent: July 23, 2013Assignee: BASF SEInventors: Gunter Lipowsky, Steffen Rissel, Volker Schliephake, Ulrich Jäger, Sylke Haremza
-
Patent number: 7541506Abstract: The invention relates to a process for the telomerization of acyclic olefins having at least two conjugated double bonds (I) or mixtures in which such olefins are present with nucleophiles (II) using a metal-carbene complex as catalyst.Type: GrantFiled: June 17, 2003Date of Patent: June 2, 2009Assignee: OXENO Olefinchemie GmbHInventors: Dirk Roettger, Ralf Jackstell, Holger Klein, Matthias Beller
-
Patent number: 7026523Abstract: The invention provides a process for the telomerization of acyclic olefins having at least two conjugated double bonds (I) or mixtures comprising such olefins by means of nucleophiles (II) using a palladium-carbene complex as catalyst.Type: GrantFiled: May 4, 2002Date of Patent: April 11, 2006Assignee: OXENO Olefinchemie GmbHInventors: Dirk Röttger, Matthias Beller, Ralf Jackstell, Holger Klein, Klaus-Diether Wiese
-
Patent number: 6914156Abstract: In yielding diacetoxybutene by feeding butadiene, acetic acid, and oxygen in the presence of a solid catalyst containing palladium, the butadiene can be efficiently reacted to produce diacetoxybutene in high yield by feeding an oxygen-containing gas containing 7 mol % or more oxygen as fine bubbles to a reaction zone containing the solid catalyst.Type: GrantFiled: April 14, 2003Date of Patent: July 5, 2005Assignee: Mitsubishi Chemical CorporationInventors: Kazuhiro Makino, Hiroshi Iwasaka, Kazuyuki Okubo, Koji Hata
-
Patent number: 6770791Abstract: Disclosed is an olefin containing stream from an oxygenate to olefin process, and a process for making olefin dimer and oligomer product from the olefin containing stream using a nickel based oligomerization catalyst. The dimer/oligomer product is optionally converted to hydroformylated product. The olefin containing stream that is used to make the higher olefin product has low levels of impurities including nitrogen, sulfur and/or chlorine.Type: GrantFiled: April 29, 2003Date of Patent: August 3, 2004Assignee: ExxonMobil Chemical Patents Inc.Inventors: Georges Mathys, John Stephen Godsmark, Marcel Janssen, Luc Roger Martens, Hubertus Joseph Beckers, Eddy Theophile Andrea Van Driessche, Raphael Frans Ivo Caers, John Richard Shutt
-
Patent number: 6534672Abstract: A catalytically active material useful to prepare vinyl acetate monomer from ethylene, acetic acid, and an oxygen-containing gas under fluid bed conditions comprises a porous microspheroidal support containing catalytically active palladium crystallites finely dispersed within the support. This catalyst material does not require incorporation of gold to maintain activity and selectivity. A process to produce a vinyl acetate fluid bed catalyst in which catalytically active small palladium crystallites are finely dispersed within the support comprises dispersing selected metal species within the support which have an affinity to palladium to form very fine crystallites of palladium. The affinity metal species may be dispersed by impregnation onto a preformed microspheroidal support or may be intimately incorporated within the support before impregnation with a soluble palladium species.Type: GrantFiled: December 4, 2001Date of Patent: March 18, 2003Assignee: The Standard Oil CompanyInventors: George Frederick Salem, Michael James Baker
-
Patent number: 6300515Abstract: The invention provides a process that includes isomerizing at least one allylic substrate having an acyloxyl group or a hydroxyl group at the allyl position thereof, to produce a corresponding allylic isomer, wherein the isomerizing is conducted in the presence of a catalyst that includes a Group VIII-X metal compound and a phosphite compound.Type: GrantFiled: April 17, 2000Date of Patent: October 9, 2001Assignee: Mitsubishi Chemical CorporationInventors: Mikael Retboll, Yoshinori Hara, Hisao Urata, Hironobu Ohno
-
Patent number: 6239324Abstract: The invention provides a chain diene compound with desirable regioselectivity, in the presence of a specific ruthenium compound. This chain diene compound is a promising raw material for terpene. It has a structure represented by the general formula (IX): wherein R1 represents H, a C1-C6 alkyl group which may be substituted or a C2-C6 alkenyl group which may be substituted, R2 represents a phenyl group which may have a C1-C4 alkyl group or a C1-C12 acyloxy group which may have a phenyl group or a naphthyl group, or a benzyl group or R2 is a hydroxy group which reversibly forms an aldehyde group through shifting of the position of the double bond adjacent to said hydroxy group. The chain diene compound is produced by reacting 2-substituted-1,3-butadienes with terminal olefins in the presence of a ruthenium compound in a hydrophilic solvent.Type: GrantFiled: August 26, 1999Date of Patent: May 29, 2001Assignee: Takasago International CorporationInventors: Mitsuhiko Fujiwhara, Takenobu Nishikawa, Yoji Hori, Toshimitsu Hagiwara, Hisao Iwai, Takashi Miura
-
Patent number: 5808136Abstract: A catalyst and method of its production for use in making vinyl acetate monomer. The carrier is impregnated with a basic solution and a solution containing gold salts and palladium salts and finally impregnated with alkali acetate. The activity and selectivity of the catalyst, its mechanical strength, the noble-metal adhesion and the dispersion of noble metal on the carrier can be improved if the carrier is impregnated in a pretreatment with salts containing as cation elements of groups IA, IIA, IIIA and IVB of the periodic table and as anions elements of group VIIA or complex anions such as nitrate, sulfate or anions of organic acids such as acetate and lactate and is subsequently dried and calcined at temperatures of at least 160.degree. C.Type: GrantFiled: January 23, 1996Date of Patent: September 15, 1998Assignee: Degussa AktiengesellschaftInventors: Thomas Tacke, Herbert Mueller, Uwe Ohlrogge, Francis P. Daly, Hans Lansink Rotgerink, Helmfried Krause
-
Patent number: 5777155Abstract: A process for producing an unsaturated glycol diester disclosed, which process comprises reacting a conjugated diene with a carboxylic acid and molecular oxygen in the presence of a solid catalyst comprising (1) palladium and (2) tellurium as active components supported on a carrier, wherein a said carrier is a solid carrier in which a proportion of the volume of pores having a pore radius in the range of from 5 to 50 nm is 80% or more relative to the total volume of pores having a pore radius in the range of from 1.8 to 10,000 nm.Type: GrantFiled: March 17, 1997Date of Patent: July 7, 1998Assignee: Mitsubishi Chemical CorporationInventors: Masato Sato, Hironobu Ohno, Nobuyuki Murai, Hiroshi Iwasaka
-
Patent number: 5429721Abstract: A process for preparing diacetoxybutene, including:reacting butadiene, acetic acid and oxygen in the presence of a palladium-based catalyst;feeding continuously the resulting reaction product into a first distillation tower;feeding continuously a withdrawn bottoms withdrawn from the first distillation tower into a second distillation tower;withdrawing bottoms containing high boiling point materials from the bottom of the second distillation tower, so that the content of the high boiling point materials in the bottoms of the second distillation tower is not more than 20 wt %;feeding continuously the withdrawn bottoms into a thin-film evaporator whose internal pressure is kept lower than the bottom pressure of the second distillation tower to carry out evaporation treatment; andrecycling the evaporated materials mainly containing diacetoxybutene into the second distillation tower.Type: GrantFiled: May 18, 1994Date of Patent: July 4, 1995Assignee: Mitsubishi Chemical CorporationInventors: Hiroaki Kandori, Nobuyuki Murai
-
Patent number: 5206396Abstract: Octyl ethers and octadienyl ethers of glucose, sucrose, bisphenol A, 4-substituted-2,2,6,6-tetramethylpiperidines are disclosed. Compositions comprised of a mixture of octyl ethers of glucose and sucrose and those containing octadienyl ethers of sugar acids and ring-opened epoxidized octadienyl ethers are also disclosed as are telomerization processes.Type: GrantFiled: July 25, 1990Date of Patent: April 27, 1993Assignee: Henkel Research CorporationInventors: Bert Gruber, Kenneth J. Weese, Steven M. Hoagland, Hans-Peter Mueller, Karlheinz Hill, Arno Behr, James R. Tucker
-
Patent number: 5177254Abstract: A method for producing an unsaturated glycol diester by reacting molecular oxygen, a carboxylic acid and a conjugated diene in the presence of a solid catalyst containing palladium and tellurium supported on a carrier, wherein an active carbon with the total pore volume of pores having radii of from 18 to 100,000 .ANG. being at least 0.45 cc/g and with the volume of pores having radii of at least 3,000 .ANG. constituting at least 50% of the total pore volume, is used as the carrier for the solid catalyst.Type: GrantFiled: February 4, 1988Date of Patent: January 5, 1993Assignee: Mitsubishi Chemical Industries LimitedInventors: Junzo Haji, Ichiro Yokotake, Takahiro Yamaguchi, Masato Sato, Nobuyuki Murai
-
Patent number: 5030792Abstract: This invention relates to a process for producing 1-octenes comprising reacting conjugated dienes and carboxylic acids in the presence of palladium, platinum or ruthenium catalysts to produce 2,7-alkadienyl esters, contacting the 2,7-alkadienyl esters with hydrogen to produce alkyl esters and subsequently pyrolyzing the alkyl esters to produce 1-octene and carboxylic acid.Type: GrantFiled: June 22, 1987Date of Patent: July 9, 1991Assignee: Shell Oil CompanyInventor: Lynn H. Slaugh
-
Patent number: 4658053Abstract: A process for the production of an ester comprises reacting an olefin with carbon monoxide, hydrogen and another ester at elevated temperature and pressure in the presence of a catalyst comprising (1) a rhodium source, (2) a ruthenium source, and (3) cobalt or zinc iodide. The product ester comprises the acid group of the ester used as reactant esterified with a hydrocarbyl group derived from the olefin, hydrogen and carbon monoxide.Type: GrantFiled: February 25, 1985Date of Patent: April 14, 1987Assignee: BP Chemicals LimitedInventor: Michael J. Green
-
Patent number: 4554375Abstract: A method for preparing 2,7-octadienyl formate by reacting 1,3-butadiene with formic acid in the presence of a platinum(II) catalyst is described. The platinum(II) catalyst is preferably platinum acetylacetonate. A reaction temperature between 50.degree. and 150.degree. C. is preferred, and carbon dioxide and a solvent may also be employed. Tetrahydrofuran and acetone are the preferred aprotic solvents.Type: GrantFiled: March 15, 1984Date of Patent: November 19, 1985Assignee: Texaco Inc.Inventors: Jiang-Jen Lin, David C. Alexander
-
Patent number: 4504676Abstract: 1,4-diacyloxybutenes are prepared by reacting a 1,3-butadiene with a carboxylic acid and oxygen in the presence of a catalyst in a reactor, by a process in which the 3,4-diacyloxybutene formed as a by-product in the reaction is separated off from the reaction mixture, and some or all of this 3,4-diacyloxybutene is recycled to the reactor.Type: GrantFiled: March 9, 1984Date of Patent: March 12, 1985Assignee: BASF AktiengesellschaftInventors: Rolf Schnabel, Gerd Kissau, Hans-Martin Weitz, Rolf Fischer
-
Patent number: 4480123Abstract: A process for preparing diacyloxyalkadienes of the formula ##STR1## where R.sup.1 to R.sup.6 are each hydrogen or a hydrocarbon radical, which contain one or more hydrocarbon radicals having one or more non-conjugated double bonds, by reacting an aliphatic triene of the formula ##STR2## in which R.sup.1 to R.sup.6 have the same meanings given above with a carboxylic acid of the formulaR.sup.7 -COOHin which R.sup.7 has the same meaning given above, in the presence of a catalyst which contains palladium, platinum or salts of these metals and in the presence of oxygen.Type: GrantFiled: July 25, 1983Date of Patent: October 30, 1984Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Hans-Martin Weitz
-
Patent number: 4468525Abstract: A process for the preparation of a diacyloxyhexadiene of the formula ##STR1## where X is R.sup.9 -CO- and R.sup.1 to R.sup.9 are hydrogen or alkyl of 1 to 3 carbon atoms, by reacting a hexatriene of the formula ##STR2## with oxygen and a carboxylic acid of the formula R.sup.9 COOH in the presence of a catalyst which contains palladium, platinum or a salt of these metals.Type: GrantFiled: April 29, 1983Date of Patent: August 28, 1984Assignee: BASF AktiengesellschaftInventors: Hans-Martin Weitz, Rolf Fischer
-
Patent number: 4399301Abstract: Methylenically-substituted undecadiene compounds having the structural formula: ##STR1## wherein X is selected from the group consisting of lower acyloxy, aryloxy having from 6 to 14 carbon atoms, lower alkoxy and hydroxy, and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15 and R.sub.16 are independently selected from the group consisting of hydrogen and lower alkyl, with the proviso that at least one of R.sub.3, R.sub.5 and R.sub.6 and at least one of R.sub.9, R.sub.10, R.sub.11 and R.sub.12 must be hydrogen, are prepared by reacting a diene having the structural formula: ##STR2## with a conjugated diene having the structural formula: ##STR3## in the presence of a rhodium/trivalent phosphorus catalyst, with the atomic ratio of the trivalent phosphorus to the rhodium therein being at least 1.5. The compounds can be hydrogenated and saponified to form known alcohols which are precursors for biodegradable detergents.Type: GrantFiled: September 13, 1979Date of Patent: August 16, 1983Assignee: Rhone-Poulenc IndustriesInventor: Didier Morel
-
Patent number: 4394290Abstract: A process for regenerating a supported catalyst for acyloxylations, which contains palladium and/or platinum and tellurium, with or without copper, wherein copper is applied to the catalyst to be regenerated.Type: GrantFiled: December 29, 1981Date of Patent: July 19, 1983Assignee: BASF AktiengesellschaftInventors: Rolf Schnabel, Hans-Martin Weitz, Rolf Fischer
-
Patent number: 4321409Abstract: A process for producing a conjugated diene monoester by reacting a gaseous mixture comprising a conjugated diene, a carboxylic acid and oxygen as reactive components, in which the fraction of said conjugated diene is preferably 12-60 mole % and the fraction of oxygen is preferably 5-30 mole %, in the gas phase in the presence of a catalyst, characterized by carrying out the reaction in the presence of a catalyst which comprises, as active components, (a) palladium, (b) at least one member selected from the group consisting of magnesium, calcium, barium, cerium, lanthanum, tungsten, copper, zinc, cadmium, boron, thallium, molybdenum, tin, lead, phosphorous, arsenic and selenium and (c) at least one alkali metal carboxylate, or a catalyst which comprises, as active components, these three components (a), (b) and (c) together with (d) at least one alkali metal halide.Type: GrantFiled: December 14, 1979Date of Patent: March 23, 1982Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Yoshinori Yoshida, Hironobu Shinohara
-
Patent number: 4287356Abstract: Vinylglycol esters are prepared by reacting butadiene with oxygen and a carboxylic acid in the gas phase or liquid phase over a supported catalyst which contains from 0.1 to 20 percent by weight of palladium and from 2.5 to 7 percent by weight of cobalt.Type: GrantFiled: November 27, 1979Date of Patent: September 1, 1981Assignee: BASF AktiengesellschaftInventors: Hans-Martin Weitz, Rolf Fischer
-
Patent number: 4262139Abstract: A process for the preparation of butenediol diacetate by reacting butadiene with oxygen and acetic acid or with a compound which liberates acetic acid under the reaction conditions, over a solid catalyst which contains a platinum metal and one or more elements of main group 5 or 6, in the presence of butanediol diacetate, butanediol monoacetate, butanediol or a mixture of these, and the use of the butenediol diacetate, thus obtained, to prepare butane-1,4-diol by hydrogenating and then hydrolyzing the diacetate.Type: GrantFiled: October 22, 1979Date of Patent: April 14, 1981Assignee: BASF AktiengesellschaftInventors: Juergen Hartig, Hans-Martin Weitz, Rolf Schnabel
-
Patent number: 4260750Abstract: A process for the telomerization of dienes with a telomerizing compound containing a mobile hydrogen atom is disclosed wherein the reaction between the diene and the telomerizing agent is effected in the presence of a catalytic system comprising a water-soluble sulfonated triaryl phosphine compound, preferably a water-soluble salt of a mono-, di-, or trisulfonated triphenyl phosphine and a transition metal compound, preferably palladium or a palladium-containing compound. Water is added either before or after the reaction is completed and the reaction products can easily be separated from the aqueous catalyst solution.Type: GrantFiled: March 13, 1980Date of Patent: April 7, 1981Assignee: Rhone-Poulenc IndustriesInventor: Emile Kuntz
-
Patent number: 4239910Abstract: In a process for the manufacture of butenediol-dicarboxylic acid esters by reacting butadiene with oxygen and a carboxylic acid in the presence of a noble metal catalyst containing platinum or palladium, the carboxylic acid is added to the reaction mixture in the form of the ester of the acid with a low molecular weight aliphatic alcohol such as methanol and the reaction is carried out under conditions under which the ester undergoes hydrolysis, or the hydrolysis is carried out before the main reaction. This enables the carboxylic acid obtained on further processing of the butenediol esters to be recycled.Type: GrantFiled: March 18, 1977Date of Patent: December 16, 1980Assignee: BASF AktiengesellschaftInventors: Hans-Martin Weitz, Rolf Platz, Juergen Hartig
-
Patent number: 4236024Abstract: Diacetoxybutene is prepared in a high yield with a high selectivity from butadiene, acetic acid and oxygen in the presence of a solid catalyst comprising sulfur, at least one noble metal selected from palladium, platinum and rhodium, and a carrier.Type: GrantFiled: February 27, 1979Date of Patent: November 25, 1980Assignee: Sumitomo Chemical Company, LimitedInventors: Teruo Matsuda, Kuniyoshi Manabe
-
Patent number: 4233455Abstract: Diesters of olefinically unsaturated 1,2- and/or 1,4-diols are prepared by reacting a conjugated diolefin, oxygen and a fatty acid, in the gas phase or liquid phase, over a solid catalyst which contains palladium and/or platinum and a further metal, which has an atomic number of from 21 to 30, from 39 to 48 or from 57 to 80, but is not a platinum metal, the catalyst having been obtained by reduction of compounds, applied to a carrier, of platinum and/or palladium and the further metal, and heating at 400.degree. C. or above.Type: GrantFiled: April 4, 1979Date of Patent: November 11, 1980Assignee: BASF AktiengesellschaftInventors: Hans-Martin Weitz, Juergen Hartig, Laszlo Marosi
-
Patent number: 4228301Abstract: In a process for preparing diacetoxybutene by subjecting butadiene, acetic acid and oxygen to reaction, the discharge gas from the reaction system or purification system, containing butadiene and/or acetic acid, is treated by contacting with diacetoxybutene and/or diacetoxybutane (absorbent) to allow butadiene and/or acetic acid to be absorbed by said absorbent. A part of the diacetoxybutene separated in a distillation tower from the reaction product solution containing diacetoxybutene produced by said three-component reaction can be used as said absorbent. In this case, butadiene and/or acetic acid can be recovered from said discharge gas by supplying the absorption solution into said distillation tower. Also usable as said absorbent is diacetoxybutane obtained by hydrogenation of diacetoxybutene.Type: GrantFiled: October 11, 1978Date of Patent: October 14, 1980Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Yoshinori Yoshida, Hironobu Shinohara
-
Patent number: 4225727Abstract: The invention relates to a process for the production of an unsaturated glycol diester by the reaction of a conjugated diene compound, a carboxylic acid and molecular oxygen in the presence of a solid catalyst. For example, 1,4-diacetoxy-2-butene is prepared at high conversion and high selectivity by reacting butadiene, molecular oxygen and acetic acid in the presence of a solid catalyst containing palladium, tellurium and at least one element selected from the group consisting of tin, germanium and lead. The product is an intermediate for the preparation of 1,4-butanediol.Type: GrantFiled: October 5, 1979Date of Patent: September 30, 1980Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Setsuo Kamiyama, Kouji Shiozawa, Yoshiharu Okumura, Katsumi Kaneko
-
Patent number: 4225729Abstract: Diacetoxybutane is prepared by a process for hydrogenating diacetoxybutene in the presence of a supported hydrogenation catalyst comprising catalytically reacting diacetoxybutene with hydrogen continuously in an insulation reaction apparatus utilizing a fixed-bed of said hydrogenation catalyst, withdrawing the reaction effluent continuously from said reaction apparatus, circulating at least a part of said reaction effluent to said reaction apparatus while controlling the temperature of influx of said reaction apparatus at a temperature lower than the temperature of efflux from said reaction apparatus by 5.degree. to 100.degree. C.Type: GrantFiled: December 2, 1976Date of Patent: September 30, 1980Assignee: Mitsubishi Chemical Industries, LimitedInventors: Jun Toriya, Ken Shiraga, Takeru Onoda, Akihisa Ohno
-
Patent number: 4182919Abstract: A reaction in a catalyst suspension system is carried out by using a reactor equipped with a filter for separating the catalyst in the reactor.Type: GrantFiled: March 16, 1978Date of Patent: January 8, 1980Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Shunsuke Mabuchi, Sadakatsu Kumoi, Kenji Tsuzuki
-
Patent number: 4152525Abstract: Disclosed is a method of recovering butadiene gas from an acetoxylation process which method comprises steps: (a) contacting a butadiene-containing gas with acetic acid to effect the absorption of butadiene in acetic acid, (b) recycling the acetic acid containing butadiene to the acetoxylation process, (c) contacting the waste gas containing acetic acid from step (a) with water to effect the absorption of acetic acid in water and (d) recycling the water containing acetic acid to hydrolysis step of the acetoxylation product.Type: GrantFiled: January 30, 1975Date of Patent: May 1, 1979Assignee: Mitsubishi Chemical Industries Ltd.Inventors: Yasuo Tanabe, Jun Toriya, Ikuo Kasahara
-
Patent number: 4150239Abstract: A process for producing 1,4-glycol diester from unsaturated glycol diesters prepared by reacting butadiene, acetic acid and oxygen or an oxygen-containing gas in the presence of a palladium catalyst or, from saturated glycol diesters prepared by hydrogenating said unsaturated glycol diesters, wherein, 1,4-glycol diester is separated from the isomer mixture of glycol diesters prepared, the residual glycol diester isomers are decomposed by heating and butadiene and/or acetic acid produced on decomposition are recycled to the process for the production of glycol diesters.Type: GrantFiled: May 27, 1977Date of Patent: April 17, 1979Assignee: Mitsubishi Chemical Industries Ltd.Inventors: Yasuo Tanabe, Jun Toriya
-
Patent number: 4142060Abstract: A process for the telomerization of dienes with a telomerizing compound containing a mobile hydrogen atom is disclosed wherein the reaction between the diene and the telomerizing agent is effected in the presence of a catalytic system comprising a water-soluble sulfonated triaryl phosphine compound, preferably a water-soluble salt of a mono-, di-, or trisulfonated triphenyl phosphine and a transition metal compound, preferably palladium or a palladium-containing compound. Water is added either before or after the reaction is completed and the reaction products can easily be separated from the aqueous catalyst solution.Type: GrantFiled: July 21, 1977Date of Patent: February 27, 1979Assignee: Rhone-Poulenc IndustriesInventor: Emile Kuntz
-
Patent number: 4131743Abstract: Unsaturated diesters are produced by a process which comprises reacting, in a flowing gaseous phase, a gaseous mixture comprising a conjugated diene, a carboxylic acid and molecular oxygen in the presence of (A) a catalyst comprising palladium, vanadium, antimony and at least one alkali metal carboxylate, or in the presence of (B) a catalyst comprising palladium, vandium, antimony, at least one alkali metal carboxylate and at least one alkali metal halide. The catalyst (A) maintains a high activity and a high selectivity for a long time. The catalyst (B), in which further the alkali metal halide is added, shows a higher activity and a higher selectivity for a longer time. And its activity and selectivity are stable and durable at high temperatures such as 160.degree. - 200.degree. C. Furthermore, the addition of the alkali metal halide suppresses combustion reaction of dienes such as butadiene remarkably.Type: GrantFiled: July 6, 1976Date of Patent: December 26, 1978Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Yoshinori Yoshida, Tutomu Kobayashi, Hironobu Shinohara, Izumi Hanari
-
Patent number: 4122285Abstract: Butenediol diacetate is manufactured by reaction of butadiene, oxygen and acetic acid over a palladium or platinum catalyst, only liquid, and no gases, being present in the reaction chamber.Type: GrantFiled: August 13, 1976Date of Patent: October 24, 1978Assignee: BASF AktiengesellschaftInventors: Hans-Martin Weitz, Ludwig Vogel, Juergen Hartig, Eckhard Hetzel
-
Patent number: 4121039Abstract: Unsaturated glycol diesters are prepared at high reaction rates, high degrees of conversion and high selectivity, by reacting a conjugated diene, a carboxylic acid and oxygen, in the presence of an improved active solid catalyst, in the liquid phase. The improved catalyst of the invention comprises palladium containing thorium as a promotor. In the preferred embodiment, butadiene and acetic acid are reacted with oxygen to produce the desired 1,4-diacetoxy-2-butene at high conversions and selectivity.Type: GrantFiled: September 26, 1977Date of Patent: October 17, 1978Assignee: GAF CorporationInventors: R. Parthasarathy, Eugene Victor Hort
-
Patent number: 4113970Abstract: 1,4-Diacyloxybutene-2 is produced with a high yield by reacting 1,3-butadiene with a carboxylic acid, for example, acetic acid, and molecular oxygen in the presence of a catalyst containing metallic palladium and at least one iodine-containing substance selected from the group consisting of iodine, iodic acid, iodates, for example, alkali metal iodates and substituted and unsubstituted ammonium iodate, and iodides, for example, hydrogen iodide, alkali metal iodide and substituted and unsubstituted ammonium iodides, the ratio in gram-atom, of iodine to palladium in the above-mentioned catalyst being 0.1 to 1.5:1.Type: GrantFiled: April 11, 1977Date of Patent: September 12, 1978Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Masanori Tanabe, Masanori Ikeda, Nobuhiro Tamura
-
Patent number: 4100361Abstract: A process for the manufacture of butenediol diacetates, especially but-2-ene-1,4-diol diacetate and but-1-ene-3,4-diol diacetate, by reacting butadiene with oxygen and acetic acid in the gas phase or liquid phase over a solid catalyst which contains platinum and at least one element of main group 5 or 6, as well as nickel.Type: GrantFiled: September 29, 1976Date of Patent: July 11, 1978Assignee: BASF AktiengesellschaftInventors: Hans-Martin Weitz, Juergen Hartig
-
Patent number: 4075413Abstract: Diacetoxybutene is prepared by a catalytic reaction of butadiene, acetic acid and oxygen or an oxygen containing gas in the presence of a supported palladium catalyst.In said reaction, the use of butadiene containing vinylcyclohexene in an amount of not more than 5,000 parts by weight per million parts by weight of butadiene and at least one polymerization inhibitor prevents the lowering of the activity of the catalyst thereby prolonging its useful life.Type: GrantFiled: June 10, 1976Date of Patent: February 21, 1978Assignee: Mitsubishi Chemical Industries LimitedInventor: Yasuo Tanabe
-
Patent number: 4075412Abstract: Diacyloxy olefins are prepared by the reaction of a conjugated diolefin with a carboxylic acid in the presence of free oxygen and a catalyst system consisting essentially of an indium compound, a halide source and an alkali metal compound.Type: GrantFiled: April 21, 1976Date of Patent: February 21, 1978Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
-
Patent number: 4057472Abstract: A fractional distillation method of separating diacetoxybutene isomers from a reaction mixture produced from the reaction of butadiene, acetic acid and molecular oxygen comprises employing a series of at least two distillation towers, one of said towers being used for distillation of water and acetic acid under a pressure of 30 - 250 Torr and a tower bottom temperature of 190.degree. - 120.degree. C and the other being used for separation of high boiling point materials under a pressure of 2 - 100 Torr and a tower bottom temperature of 190.degree. - 120.degree. C, the temperature of all tower bottoms being from 190.degree. - 120.degree. C.Type: GrantFiled: February 6, 1976Date of Patent: November 8, 1977Assignees: Noboru Haji, Mitsubishi Chemical Industries Ltd.Inventors: Jun Toriya, Masato Sato, Ken Shiraga, Setsuo Matsunaga