Two Identical Or Diverse Alkyl Groups Bonded Directly To The -o-c(=o)o- Group (e.g., Dimethyl Carbonate, Methyl Ethyl Carbonate, Etc.) Patents (Class 558/277)
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Patent number: 5142086Abstract: A method for making diphenyl carbonate free of color bodies is provided by reacting an organic hydroxy compound, such as phenol with carbon monoxide and oxygen in the presence of an effective amount of a palladium catalyst, in the form of a palladium material which is used in combination with a quaternary ammonium salt, an inorganic cocatalyst, such as cobalt diacetate and an organic cocatalyst such as benzophenone or 1,10-phenanthroline. Recycling of catalyst values is also provided.Type: GrantFiled: April 1, 1991Date of Patent: August 25, 1992Assignee: General Electric CompanyInventors: Joseph A. King, Jr., Terry E. Krafft, Gary R. Faler
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Patent number: 5140044Abstract: A UCN-1028D derivative represented by the formula: ##STR1## has protein kinase C inhibitory activity and is expected to be used as an active ingredient in anti-tumor agents, etc.Type: GrantFiled: March 27, 1990Date of Patent: August 18, 1992Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Teruo Kishi, Hiromitsu Saito, Hiroshi Sano, Isami Takahashi, Tatsuya Tamaoki
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Patent number: 5132447Abstract: A method is provided for making an organic carbonate such as, a diaryl carbonate by heating a mixture under elevated conditions of temperature and pressure comprising an arylhydroxy compound, such as phenol, carbon monoxide and oxygen in the presence of a palladium catalyst and carbon dioxide as a desiccant.Type: GrantFiled: July 1, 1991Date of Patent: July 21, 1992Assignee: General Electric CompanyInventor: Joseph A. King, Jr.
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Patent number: 5118818Abstract: Organic carbonates: ##STR1## and cyclic organic carbonates: ##STR2## are prepared by reacting an alcohol (R--OH), or respectively a diol (HO--R'--OH), with carbon monoxide, in the presence of:a halogen, ora halogen and/or a halide ion and an oxidizing agent.Type: GrantFiled: March 6, 1991Date of Patent: June 2, 1992Assignee: Enichem Synthesis S.p.A.Inventors: Daniele Delledonne, Franco Rivetti, Ugo Romano
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Patent number: 5093513Abstract: A lower alkanol, such as methanol is oxycarbonylated with carbon monoxide and oxygen to yield e.g. dimethyl carbonate at 50.degree. C.-125.degree. C. and 300-1500 psig in the presence of as catalyst, a functionalized inorganic oxide substrate (such as silica gel) typically bearing on the surface thereof a ligand of ethyl formate and 3-aminopropyl triethoxy silane--which has been reacted with a metal salt such as CuCl.sub.2.Type: GrantFiled: January 22, 1988Date of Patent: March 3, 1992Assignee: Texaco Inc.Inventors: Robert A. Sawicki, Harry Chafetz
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Patent number: 5089650Abstract: Disclosed herein is a process for producing a carbonic acid ester by reacting alcohol, carbon monoxide, and oxygen with one another in the presence of a copper compound alone or together with a platinum group metal compound and a reaction accelerator, characterized in that (I) the reaction is carried out in a nitrile compound or amide compound as a solvent, (II) the reaction is carried out in the presence of a reaction accelerator which consists of a quaternary phosphonium halide and a quaternary phosphonium weak acid salt or quaternary phosphonium alkoxide, and/or (III) the reaction is carried out in the presence of a quinoid compound or a compound that changes into a quinoid compound under the reaction conditions.Type: GrantFiled: September 1, 1987Date of Patent: February 18, 1992Assignee: Daicel Chemical Industries, Ltd.Inventors: Shigeru Yokota, Hiroshi Koyama, Hidetaka Kojima
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Patent number: 5015753Abstract: Poly(alkylene carbonate) monoahls and polyahls useful as nonionic surfactants and having a poly(alkylene carbonate) backbone are prepared by reacting an oligomeric poly(alkylene carbonate) polyahl with a compound having mono- or difunctional active hydrogen moieties, such as alcohols, carboxylic acids, mercaptans, amides, primary or secondary amines, or substituted phenols, optionally in the presence of a catalyst, under transesterification conditions.Type: GrantFiled: November 13, 1989Date of Patent: May 14, 1991Assignee: The Dow Chemical CompanyInventor: Robert F. Harris
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Patent number: 5004827Abstract: A process for the preparation of dihydrocarbyl carbonates comprising contacting an alkanol such as methanol, carbon monoxide and oxygen with a heterogeneous catalyst which comprises a metal halide such as cupric chloride or a mixed metal halide such as cupric chloride/potassium chloride impregnated on an appropriate support such as activated carbon; and a process for reactivating metal halide catalysts supported on porous carrier materials comprising drying and then contacting the supported catalysts with a gaseous stream of hydrogen halide for a period of time which is sufficient to convert all of the metal present in whatever form to the corresponding metal halide.Type: GrantFiled: September 17, 1987Date of Patent: April 2, 1991Assignee: The Dow Chemical CompanyInventor: Gerald L. Curnutt
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Patent number: 5001252Abstract: An organic carbonate such as dimethyl carbonate is prepared by reacting an alcohol such as methanol with carbon monoxide and oxygen in the presence of a catalyst system containing Cu(OMe)Cl as catalyst and a urea or a mixture of ureas as a cosolvent for the catalyst system.Type: GrantFiled: December 11, 1987Date of Patent: March 19, 1991Assignee: Texaco Inc.Inventor: Ajit K. Bhattacharya
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Patent number: 4973728Abstract: Aromatic carbonates useful for the preparation of high molecular weight polycarbonate resins are prepared by reacting methanol, carbon monoxide and oxygen to prepare dimethyl carbonate; reacting a methyl silyl ether with a phenol or bisphenol to prepare an aryl silyl ether, and reacting the dimethyl carbonate and aryl silyl ether to prepare an aromatic carbonate.Type: GrantFiled: August 12, 1987Date of Patent: November 27, 1990Assignee: The Dow Chemical CompanyInventors: Hendrik E. Tuinstra, Cynthia L. Rand, Edmund P. Woo
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Patent number: 4943626Abstract: Polyether active hydrogen compounds having at least two terminal active hydrogen groups on primary carbon atoms are prepared by (a) forming polyoxyalkylene molecules each having at least one active hydrogen precursor, (b) linking at least two of the polyoxyalkylene molecules, and (c) converting the active hydrogen precursor groups to active hydrogen groups on primary carbon atoms. The polyoxyalkylene molecule is formed by exposing a reaction mixture comprising at least one alkylene oxide and at least one protective initiator to conditions effective for the polymerization of the alkylene oxides. Linking is accomplished at polyether chain ends distal to the protected active hydrogen precursor groups, such that the active hydrogen precursors remain on the linked polyether chains until they are converted to active hydrogen groups.Type: GrantFiled: July 29, 1988Date of Patent: July 24, 1990Assignee: The Dow Chemical CompanyInventors: James E. McGrath, Youngtai Yoo, Robert B. Turner, Diane M. Lewis
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Patent number: 4898946Abstract: A process is described for the preparation of N-allyl-2,2,6,6-tetraalkyl-piperidine derivatives which involves reaction of the corresponding 2,2,6,6-tetraalkyl-piperidine with an allylic carbonate in the presence of palladium catalysts. The products which are thus obtained are useful as polymer stabilizers and chemical intermediates.Type: GrantFiled: June 3, 1987Date of Patent: February 6, 1990Assignee: Enichem Synthesis S.p.A.Inventors: Silvestro Costanzi, Damiano Gussoni, Luciano Pallini
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Patent number: 4820857Abstract: The novel compound .alpha.-bromodiethylcarbonate, novel methods for the preparation thereof, its use in the preparation of 1-ethoxycarbonyloxyethyl esters of penicillins and cephalosporins, and improvements in the method for preparing such esters.Type: GrantFiled: April 13, 1988Date of Patent: April 11, 1989Assignee: Astra Lakemedel AktiebolagInventors: Derek R. Palmer, Robert G. Tyson
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Patent number: 4816595Abstract: A process for preparing carbonate esters by the oxidative carbonylation of an alcohol is provided. The process comprises reacting an alcohol with carbon monoxide in the presence of a dihydrocarbyl peroxide the process being characterized by the fact that the carbon monoxide pressure at the reaction temperature is less than 15 bars and by the fact that a catalyst comprising a platinum group metal and a copper compound is employed. The process is useful for preparing dimethyl carbonate from methanol and carbon monoxide.Type: GrantFiled: October 14, 1986Date of Patent: March 28, 1989Assignee: British Petroleum Company p.l.c.Inventors: Andrew R. Lucy, George E. Morris
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Patent number: 4808745Abstract: The invention relates to a process for the preparation of 1-bromoethyl hydrocarbonyl carbonates, characterized in that anhydrous hydrobromic acid is reacted with a vinyl hydrocarbonyl carbonate of formula ##STR1## in which R denotes a saturated, substituted or unsubstituted C.sub.1 -C.sub.12 aliphatic radical or C.sub.5 -C.sub.24 alicyclic radical, or a substituted or unsubstituted aromatic radical, at a temperature between 10.degree. and 100.degree. C.The invention also relates to the new 1-bromoethyl hydrocarbonyl carbonates of formula: ##STR2## These carbonates are particularly sought after for introducing a carbonate group into a molecule.Type: GrantFiled: March 23, 1987Date of Patent: February 28, 1989Assignee: Societe Nationale des Poudres et ExplosifsInventors: Thierry Malfroot, Marc Piteau, Jean-Pierre Senet
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Patent number: 4785130Abstract: An organic carbonate such as dimethyl carbonate is prepared by reacting an alcohol such as methanol and carbon monoxide in the presence of a catalyst system containing Cu(OMe)Cl as catalyst and boron trifluoride, calcium chloride, benzyltriethylammonium chloride, etc. as promoters.Type: GrantFiled: September 20, 1984Date of Patent: November 15, 1988Assignee: Texaco Inc.Inventor: Ajit K. Bhattacharya
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Patent number: 4761467Abstract: An organic carbonate such as dimethyl carbonate is prepared by reacting an alcohol such as methanol with carbon monoxide and oxygen in the presence of a catalyst system containing Cu(OMe)Cl as a catalyst and a pyridine compound as a ligand of the catalyst system.Type: GrantFiled: October 21, 1985Date of Patent: August 2, 1988Assignee: Texaco Inc.Inventor: Ajit K. Bhattacharya
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Patent number: 4734518Abstract: A process is disclosed for the cosynthesis of ethylene glycol and dimethyl carbonate by reacting methanol and ethylene carbonate in the presence of a homogeneous catalyst from the group consisting of soluble miscible tertiary phosphines arsines, and stibines and soluble, miscible bivalent sulphur and selenium compounds.Type: GrantFiled: January 12, 1987Date of Patent: March 29, 1988Assignee: Texaco Inc.Inventor: John F. Knifton
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Patent number: 4697032Abstract: The invention relates to a process for the preparation of 1-bromoethyl hydrocarbonyl carbonates, characterized in that anhydrous hydrobromic acid is reacted with a vinyl hydrocarbonyl carbonate of formula ##STR1## in which R denotes a saturated, substituted or unsubstituted C.sub.1 -C.sub.12 aliphatic radical or C.sub.5 -C.sub.24 alicyclic radical, or a substituted or unsubstituted aromatic radical, at a temperature between 10.degree. and 100.degree. C.The invention also relates to the new 1-bromoethyl hydrocarbonyl carbonates of formula: ##STR2## These carbonates are particularly sought after for introducing a carbonate group into a molecule.Type: GrantFiled: November 8, 1985Date of Patent: September 29, 1987Assignee: Societe Nationale des Poudres et ExplosifsInventors: Thierry Malfroot, Marc Piteau, Jean-Pierre Senet
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Patent number: 4691041Abstract: A process is disclosed for the preparation of ethylene glycol and dimethyl carbonate by reacting methanol and ethylene carbonate in the presence of a series of heterogenous catalyst systems including ion exchange resins with tertiary amine, quaternary ammonium, sulfonic acid and carboxylic acid functional groups, alkali and alkaline earth silicates impregnated into silica and ammonium exchanged zeolites.Type: GrantFiled: January 3, 1986Date of Patent: September 1, 1987Assignee: Texaco Inc.Inventors: Roger G. Duranleau, Edward C. Y. Nieh, John F. Knifton
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Patent number: 4689422Abstract: A novel ligand system useful in preparation of dimethyl carbonate is prepared by complexing a metal salt such as cuprous chloride Cu.sub.2 Cl.sub.2 with a ligand formed by reacting a carbonyl-containing compound such as ethyl formate with an organosilicon compound such as ethyl formate with an organosilicon compound containing alkoxy and amine functionality, such as 3-aminopropyltriethoxysilane or [3-(2-aminoethyl)aminopropyl]trimethoxysilane.Type: GrantFiled: December 27, 1985Date of Patent: August 25, 1987Assignee: Texaco Inc.Inventors: Robert A. Sawicki, Harry Chafetz
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Patent number: 4681967Abstract: A process for the transesterification of a carboxylic or carbonic acid ester comprises reacting the carboxylic or carbonic acid ester under transesterification conditions with an alcohol in the presence, as catalyst, of either (i) a Group V element-containing Lewis base and an epoxide or (ii) a cyclic amidine.The Lewis base can be an organic compound containing trivalent phosphorus or nitrogen and can be an amine, for example an amidine.The process can be operated in the liquid phase at a temperature of from 15.degree. to 150.degree. C., and the catalyst is employed in solution.Preferred catalysts are those where the cyclic amidine forms part of a fused ring system containing six and five membered rings, six and seven membered rings or two six membered rings.Type: GrantFiled: August 23, 1985Date of Patent: July 21, 1987Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4663477Abstract: A process is provided for the utilization of dialkyl carbonates formed as by-products in a continuous process for the synthesis of oxalic acid esters from nitrous acid esters and carbon monoxide and wherein the esters are subsequently used as intermediates in the production of commercially useful products, such as ethylene glycol. The process comprises contacting a mixture containing the by-product comprised of a dialkyl carbonate with an aqueous solution of a metal carbonate under hydrolyzing conditions whereby the dialkyl carbonate is converted to the corresponding alkanol and the metal carbonate is converted to metal bicarbonate. Upon distillation of the alkanol from the mixture the bicarbonate is converted back to the metal carbonate which can then be recycled from the bottoms to the hydrolyzing zone for use in further hydrolysis of by-product. The alkanol is recycled for use in the continuous process.Type: GrantFiled: March 27, 1986Date of Patent: May 5, 1987Assignee: Union Carbide CorporationInventors: John W. Crandall, James E. Deitzler, Louis A. Kapicak, Fedor Poppelsdorf
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Patent number: 4661609Abstract: A process is disclosed for the cosynthesis of ethylene glycol and dimethyl carbonate by reacting methanol and ethylene carbonate in the presence of a catalyst selected from the group consisting of zirconium, titanium and tin.Type: GrantFiled: July 31, 1986Date of Patent: April 28, 1987Assignee: Texaco Inc.Inventor: John F. Knifton
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Patent number: 4659855Abstract: Certain novel aryl sulfonyl fluorides, their preparation, and their use in inhibiting serine proteases with chymotrypsin-like and elastase-like specificity.Type: GrantFiled: May 9, 1983Date of Patent: April 21, 1987Assignee: Georgia Tech Research CorporationInventor: James C. Powers
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Patent number: 4652667Abstract: A process is provided for the transesterification of carbonate esters and carboxylic acid esters at elevated temperatures and in the presence of an effective amount of an amidine compound.Type: GrantFiled: January 18, 1985Date of Patent: March 24, 1987Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4652665Abstract: The invention relates to new .alpha.-chlorinated carbonates characterized in that their formula is: ##STR1## in which X is a fluorine, chlorine or bromine atom and R.sup.1 is different from the ##STR2## group and represents; a substituted or non-substituted, saturated or unsaturated, aliphatic, araliphatic, primary, secondary, tertiary or cycloaliphatic radical.These .alpha.-chlorinated carbonates are prepared by the action of a compound of formula R.sup.1 OH on a chloroformate of formula: ##STR3## in a solvent medium in the presence of an acid scavenger which is added after the two preceding compounds.They are used to block the amine function of amino acids. The .alpha.-chlorinated carbonate and amino acid are reacted in a solvent medium at a temperature of -5.degree. to 100.degree. C. in the presence of an acid scavenger. Blocked amines are very useful in peptide synthesis.Type: GrantFiled: February 14, 1985Date of Patent: March 24, 1987Assignee: Societe Nationale des Poudres et ExplosifsInventors: Gerard Barcelo, Jean-Pierre Senet, Gerard Sennyey
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Patent number: 4644078Abstract: A process for the production of a dialkyl carbonate, e.g. dimethyl carbonate, or a dialkyl oxalate, e.g. dimethyl oxalate, from butane, oxygen, carbon monoxide and an alcohol is provided in a series of integrated process steps. In the case of a dialkyl oxalate, the product can be hydrogenated further to produce an ether of ethylene glycol.Type: GrantFiled: June 4, 1985Date of Patent: February 17, 1987Assignee: The British Petroleum Company p.l.c.Inventors: George E. Morris, Gillian Wainhouse
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Patent number: 4638076Abstract: An organic carbonate such as dimethyl carbonate is prepared by reacting an alcohol such as methanol with carbon monoxide oxygen in the presence of a catalyst system containing Cu(OMe)Cl as a catalyst and a phosphoramide as an additive for the catalyst system.Type: GrantFiled: August 16, 1985Date of Patent: January 20, 1987Assignee: Texaco Inc.Inventor: Ajit K. Bhattacharya
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Patent number: 4636576Abstract: An organic carbonate such as dimethyl carbonate is prepared by reacting an alcohol such as methanol with carbon monoxide and oxygen in the presence of a catalyst system containing Cu(OMe)Cl as catalyst and a cyclic amide as an additive or cosolvent for the catalyst system.Type: GrantFiled: September 30, 1985Date of Patent: January 13, 1987Assignee: Texaco Inc.Inventors: Ajit K. Bhattacharya, John T. Nolan, Jr.
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Patent number: 4625044Abstract: The invention is a composition which comprises a nitrogen-containing coordination compound copper hydrocarbyloxy halide complex supported on activated carbon. This composition is useful as a catalyst for the preparation of dihydrocarbyl carbonates from alcohols, carbon monoxide and oxygen.Type: GrantFiled: May 21, 1984Date of Patent: November 25, 1986Assignee: The Dow Chemical CompanyInventor: Gerald L. Curnutt
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Patent number: 4604242Abstract: This invention is a process for the preparation of a symmetrical or unsymmetrical dihydrocarbyl carbonate which comprises contacting an aliphatic, cycloaliphatic or di(aryl-substituted aliphatic) alcohol or mixtures thereof with carbon monoxide and oxygen in the presence of a catalytic amount of bis((2,4-pentanedianato)copper (II) methoxide) and a cocatalytic amount of a basic nitrogen-containing coordination compound under conditions such that a symmetrical or unsymmetrical dihydrocarbyl carbonate is prepared.Type: GrantFiled: March 19, 1984Date of Patent: August 5, 1986Assignee: The Dow Chemical CompanyInventors: A. Dale Harley, Jerald L. Curnutt, David T. Doughty
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Patent number: 4582645Abstract: A solution of a di-alkyl carbonate, e.g. dimethyl carbonate, in the corresponding alcohol, e.g. methanol, is concentrated by contacting the solution with a hydrophobic zeolite e.g. silicalite. The di-alkyl carbonate is absorbed preferentially. Where the solution also contains water, e.g. as in the case of the products from certain di-alkyl carbonate synthesis reactions, the water can be removed using a hydrophilic zeolite prior to recycle of the alcohol.Type: GrantFiled: September 10, 1984Date of Patent: April 15, 1986Assignee: Imperial Chemical Industries PLCInventor: Michael S. Spencer