Acyclic Monohydric Alcohol Moiety Patents (Class 560/265)
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Patent number: 5750571Abstract: Methods for treating cystic fibrosis are described. The methods involve the administration of a protein enhancing agent, differentiating agent and/or carboxy-compound to a subject afflicted with cystic fibrosis such that mutant cystic fibrosis transmembrane regulator protein present within cystic fibrosis-associated cells becomes functional. Other aspects described include therapeutic compositions and packaged drugs.Type: GrantFiled: December 23, 1996Date of Patent: May 12, 1998Assignee: Genzyme CorporationInventors: Seng Hing Cheng, Shaona Lee Fang, Henry Hoppe, IV, Alan Edward Smith
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Patent number: 5723652Abstract: The invention is to provide an asymmetric reaction catalyst useful for the production of medical or agricultural chemicals or intermediates thereof. The catalyst comprises an optically active monophosphino carboxylic acid derivative represented by the formula (I): ##STR1## where R.sup.1 represents a C.sub.1-6 alkyl group or phenyl group which may be optionally substituted with a C.sub.1-4 alkyl group or C.sub.1-4 alkoxy group,R.sup.2 represents a C.sub.1-4 alkyl group,R.sup.3 and R.sup.4 each represents independently a hydrogen atom, C.sub.1-4 alkyl group or phenyl group which may be optionally substituted with a C.sub.1-4 alkyl or C.sub.1-4 alkoxy group and a transition metal compound.Type: GrantFiled: June 26, 1996Date of Patent: March 3, 1998Assignee: Nissan Chemical Industries, Ltd.Inventor: Tohru Minami
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Patent number: 5719311Abstract: An improved process for the esterification of carboxylic acid and alcohols into carboxylic ester is disclosed. It comprises the steps of: (a) charging the esterification reactants into a fixed bed reactor under a predetermined reaction condition; and (b) reacting the esterification reactants in the fixed bed reactor. The fixed bed reactor contains acidic catalysts that are present in a solid phase, and the reaction condition is controlled such that (i) the reactants and the products co-exist in a gas-liquid two-phase equilibrium in the fixed bed reactor and that (ii) at least one component of the reactants is present in one phase and at least one component of the products is present in another phase. Because a phase change is always taking place concurrently with the esterification reaction; the reaction stream is maintained at a relatively uniform temperature.Type: GrantFiled: November 19, 1996Date of Patent: February 17, 1998Assignee: Industrial Technology Research InstituteInventors: Kuo-Ching Wu, Wen-Chyi Lin, Chiung-Hui Huang, Po-Yu Chen
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Patent number: 5674898Abstract: Methods and compositions for treating Cystic Fibrosis by mobilizing mutant forms of CFTR, which retain at least some functional activity, to the plasma membrane where they can mediate chloride ion transport are disclosed.Type: GrantFiled: June 7, 1993Date of Patent: October 7, 1997Assignee: Genzyme CorporationInventors: Seng Hing Cheng, Shaona Lee Fang, Henry Hoppe, IV, Alan Edward Smith
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Patent number: 5405992Abstract: A process for the continuous esterification of at least one alcohol and at least one carboxylic acid to form at least one ester and water, and the concurrent separation of the esterification products has been developed. The process uses a solid bed which as a catalyst for esterification and as an adsorbent for at least one of the products. The process preferably operates in the simulated moving bed mode. A specific embodiment of the invention is one where the simulated moving bed is a homogeneous mixture of at least one solid effective as an esterification catalyst and at least one solid effective as an ester or water adsorbent. Another specific embodiment is one where the simulated moving bed is a strongly acidic macroreticular polymeric resin effective both as an esterification catalyst and as an adsorbent for at least one esterification product.Type: GrantFiled: April 28, 1994Date of Patent: April 11, 1995Assignee: UOPInventors: Gregory A. Funk, James R. Lansbarkis, Ajay K. Chandhok
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Patent number: 5395961Abstract: Disclosed is a method of reducing the decomposition of liquid acetates and increasing their storage life. A soluble amine having a pH in water between 9 and 12 is added to the acetate. Also disclosed is a composition of about 1 to about 50 ppm of the amine in the acetate.Type: GrantFiled: July 26, 1993Date of Patent: March 7, 1995Assignee: Occidental Chemical CorporationInventors: J. Steven Qi, Garra C. Lester
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Patent number: 5371279Abstract: Disclosed is a method of making a liquid ether acetate. After reacting acetic acid with the corresponding ether alcohol, the resulting mixture of ether acetate, water, acetic acid, and ether alcohol is, with no distillation, contacted with alumina. Particular ether acetates that can be treated include ethylene glycol monobutyl ether acetate and diethylene glycol monobutyl ether acetate. The treated acetates are more stable to hydrolysis after they have been passed over a bed of alumina.Type: GrantFiled: March 21, 1994Date of Patent: December 6, 1994Assignee: Occidental Chemical CorporationInventors: Jian S. Qi, Garra C. Lester
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Patent number: 5349075Abstract: The invention provides a process for the esterification of a C.sub.2 -C.sub.24 monocarboxylic acid with a C.sub.1 -C.sub.5 monoalcohol in a reactor at an increased reaction temperature and increased pressure which is carried out in the absence of any esterification catalyst while continuously feeding in the alcohol during the reaction and removing a gaseous alcohol/water mixture. Preferably the process is carried out in countercurrent in column reactor which is packed or contains plates. The reaction temperature is usually between 200.degree. C. and 260.degree. C. at a pressure between 0.5 and 1.5 MPa. There is a C.sub.6 -C.sub.20 monocarboxylic acid and monoalcohol a C.sub.1 -C.sub.3 monoalcohol. More preferably the process is carried in two steps with a first step as described above and a second step in which further reaction to a conversion of at least 99% is carried out in the presence of an esterification catalyst at a temperature below 100.degree. C.Type: GrantFiled: December 21, 1990Date of Patent: September 20, 1994Assignee: Unilever Patent Holdings B.V.Inventors: Hendrikus J. van den Berg, Robbert Klok
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Patent number: 5336793Abstract: A method of preparing carboxylic acids or esters thereof by the oxidative cleavage of unsaturated fatty acids or esters thereof is carried out in a two-phase aqueous-organic system in which the organic phase contains the unsaturated fatty acid and/or the esters thereof and the aqueous phase contains hydrogen peroxide. The oxidative cleavage is carried out in the presence of a catalytic system including a catalyst belonging to the group constituted by tungstic and molybdic acids and alkaline salts thereof, and an onium salt which acts as a phase-transfer agent for the catalyst, and has the formula:(R.sub.2 R.sub.3 R.sub.4 R.sub.5 M).sup.+ Y.sup.-in which R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent hydrocarbon groups of which at least one must have more than 10 carbon atoms,M is N or P, andY.sup.- is an inorganic anion.Type: GrantFiled: December 10, 1992Date of Patent: August 9, 1994Assignee: Novamont S.p.A.Inventors: Andrea Gardano, Giampiero Sabarino, Marco Foa
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Patent number: 5334751Abstract: Disclosed is a process for making ethyl acetate which comprises reacting in a reaction zone ethyanol and molecular oxygen in the presence of a solid catalyst containing the elements and proportions indicated by the empirical formulaPd.sub.a M.sub.b TiP.sub.c O.sub.x (formula 1)where M is selected from Cd, Au, Zn, Tl, alkali metals and alkalineearth metals,a is from 0.0005 to 0.2b is from zero to 3ac is 0.5 to 2.5, andx is a value sufficient to satisfy the valence requirements ofthe other elements present, andwherein said catalyst contains crystalline TiP.sub.2 O.sub.7.Type: GrantFiled: April 28, 1992Date of Patent: August 2, 1994Assignee: The Standard Oil CompanyInventors: Michael F. Lemanski, Joseph B. Hazen, Patricia R. Blum
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Patent number: 5312966Abstract: There is disclosed a process for efficiently producing a carboxylic acid ester and formamide by reacting a carboxylic acid amide with a formic acid ester or with an alcohol and carbon monoxide in the presence of a strongly basic anion-exchange resin. By the use of the strongly basic anion-exchange resin as the catalyst, the process of the present invention enables the efficient production of the carboxylic acid ester as well as formamide from the Carboxylic acid amide and Formic acid ester, etc. with a high selectivity under mild reaction conditions and facilitates the separation of the catalyst from the reaction product, thereby greatly enhancing the industrial significance of itself.Type: GrantFiled: September 14, 1992Date of Patent: May 17, 1994Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takafumi Abe, Yoshiyuki Nishide, Nobuyuki Muro, Hirofumi Higuchi
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Patent number: 5304675Abstract: An ester product consisting essentially of the acylation product of a mixture of near linear aliphatic 1-alkanols, said alkanols containing six to twenty carbon atoms and having a methyl to methylene branch ratio less than 0.25. These novel esters can be further converted to valuable 1-alkenes by pyrrolysis. In the preferred embodiments, esters are derived by acylation of C.sub.9 -C12 1-alkanols having a methyl to methylene branch ratio less than 0.18.In the preferred method of synthesizing the esters, acylation is carried out using aliphatic carboxylic acid, anhydride, halide or ester as acylating agent, wherein the agent has 2 to 20 carbon atoms. For instance, the acylating agent may comprise acetic anhydride and to produce acetate esters.Type: GrantFiled: December 11, 1990Date of Patent: April 19, 1994Assignee: Mobil Oil CorporationInventor: Catherine S. H. Chen
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Patent number: 5302748Abstract: An improved process for preparing esters of an alcohol and a carboxylic acid employing sulfuric acid in an amount effective to both catalyze the reaction and to remove or immobilize the water of reaction whereby an ester is provided in increased yield and purity. Esters of long chain acids are useful for the preparation of diketones which find utility as metal extractants.Type: GrantFiled: February 11, 1993Date of Patent: April 12, 1994Assignee: Henkel CorporationInventor: Leroy O. Krbechek
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Patent number: 5302747Abstract: A method and apparatus for producing esters without the aid of a conventional acid catalyst. A mixture of a monohydric aliphatic alcohol and a lower carboxylic acid is provided in a reaction vessel equipped with a fractionating column connected to a condenser and a collecting vessel. Heating means and a device for passing small bubbles of gas through the reactants are included. The alcohol/carboxylic acid mixture is maintained at a temperature of at least about the boiling point of the alcohol, but below about the boiling point of the carboxylic acid, and a gas inert to the esterification reaction is bubbled through the mixture to remove the esterification product therein formed. The removed vapors are collected and condensed, and the esterification product is recovered in high conversion and purity.Type: GrantFiled: August 24, 1992Date of Patent: April 12, 1994Assignee: Purdue Research FoundationInventors: Philip E. Nelson, Athula Ekanayake
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Patent number: 5296630Abstract: A process for continuously producing an anhydrous methyl acetate/methanol mixture by esterifying acetic acid and methanol in the presence of an acidic esterification catalyst is indicated, which comprises carrying out the esterification in a distillation column having n=20 to 50 distillation trays,a) the acetic acid being fed together with the catalyst to a distillation tray which is at a distance of 0.5 n to 0.8 n from the still bottom,b) feeding 50 to 80% by weight of the total methanol to the still bottom and the remaining methanol to a distillation tray which is 2 to 10 trays above the acetic acid feed tray,c) feeding methanol and acetic acid into the distillation column at a molar ratio of (1.5 to 3):1,d) setting a reflux ratio of (0.75 to 1.5):1,e) taking off the anhydrous methyl acetate/methanol mixture at the top of the column andf) a water/methanol/acetic acid bottom product with the catalyst from the still bottom.Type: GrantFiled: March 2, 1990Date of Patent: March 22, 1994Assignee: Hoechst AktiengesellschaftInventors: Heinz Erpenbach, Klaus Gunther, Gerog Kohl
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Patent number: 5278338Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.3 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 40.degree. C.Type: GrantFiled: November 4, 1992Date of Patent: January 11, 1994Assignee: Ethyl CorporationInventor: Rhonda L. Trace
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Patent number: 5233078Abstract: The invention relates to a process for preparing dialkyl malonates by ozonolysis of diketene, subsequent catalytic hydrogenation and esterification of the reaction products, the by-products being alkyl formates and dialkyl acetals.Type: GrantFiled: June 4, 1992Date of Patent: August 3, 1993Assignee: BASF AktiengesellschaftInventors: Ludwig Schuster, Klaus Halbritter
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Patent number: 5231221Abstract: Compounds of the formula ##STR1## can advantageously be prepared by reacting compounds the formula II ##STR2## in which the substituents R.sup.1 -R.sup.4 have the meanings given, with the anhydride of the formula III ##STR3## in the presence of dimethyl sulfoxide and the acid corresponding to the anhydride of the formula III.Type: GrantFiled: March 18, 1991Date of Patent: July 27, 1993Assignee: Hoechst AktiengesellschaftInventors: Winfried Hertzsch, Gerhard Jahne
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Patent number: 5231222Abstract: An improved esterification process for producing volatile product esters by reacting a lower linear hydrocarbyl carboxylic acid with an alcohol containing from 2 to 10 carbon atoms, in a substantially non-aqueous medium, the improvement comprising minimizing the amount of acidic sulfate contained in the product ester by employing as the esterification catalyst a long chain alkylbenzene sulfonic acid catalyst, the alkyl radical containing from 8 to 20 carbon atoms, or mixtures of such catalysts.Type: GrantFiled: July 2, 1991Date of Patent: July 27, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Anthony J. Papa, David R. Bryant
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Patent number: 5221765Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.2 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 75.degree. C. to about 200.degree. C.Type: GrantFiled: January 24, 1992Date of Patent: June 22, 1993Assignee: Ethyl CorporationInventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
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Patent number: 5202468Abstract: The object of the invention is a process for the preparation of methyl acetate starting from the methyl formate, characterized in that methyl formate is converted at a temperature of 170.degree. to 220.degree. C. in the presence of:a) a catalyst based on rhodium,b) an iodine-containing promoter selected from among the alkaline, alkaline earth, phosphonium or ammonium iodides and the mixtures of covalent compounds of iodine supplemented with a phosphine or a tertiary amine.c) a solvent selected from a cyclic N-alkyl amide.Type: GrantFiled: June 9, 1992Date of Patent: April 13, 1993Assignee: SollacInventors: Jean A. Cordier, Francis P. Petit, Yves Castanet, Serge Melloul, Andre Mortreux
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Patent number: 5194668Abstract: Carboxylic acid esters and formamide are efficiently obtained by reacting carboxylic acid amides and formic acid esters, or by reacting carboxylic acid amides, alcohols and carbon monoxide in the presence of a dehydrated condensate of carboxylic acid amide with an alkali metal hydroxide or an alkaline earth metal hydroxide catalyst.Type: GrantFiled: June 8, 1990Date of Patent: March 16, 1993Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hideo Ikarashi, Hirofumi Higuchi, Koichi Kida
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Patent number: 5151547Abstract: Disclosed is a process for producing an organic carboxylic acid ester from an organic carboxylic acid corresponding to said organic carboxylic acid ester and an alcohol by esterification reaction in gas phase which comprises carrying out the reaction with continuously or intermittently feeding sulfuric acid as a catalyst component in the presence of a catalyst carrier. The sulfuric acid may be previously supported on the catalyst carrier.Type: GrantFiled: March 4, 1991Date of Patent: September 29, 1992Assignee: Sumitomo Chemical Co., Ltd.Inventors: Hiroshi Sato, Hiroshi Yoshioka
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Patent number: 5149861Abstract: Trialkylamines and methyl formate are recovered from reaction mixtures obtained in the preparation of trimethylolalkanes by reaction of n-alkanals with from 2.2 to 4.5 moles of formaldehyde in aqueous solution in the presence of from 0.6 to 3 mole of trialkylamine, each quantity based on 1 mole of alkanal, and subsequent hydrogenation in a process wherein the crude reaction mixturea) is heated to from 100.degree. to 200.degree. C.Type: GrantFiled: March 1, 1991Date of Patent: September 22, 1992Assignee: BASF AktiengesellschaftInventors: Franz Merger, Peter Hettinger, Leopold Hupfer, Juergen Paetsch, Heribert Deck, Heinz Auer, Erwin Brunner
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Patent number: 5147929Abstract: The invention relates to a process for mild esterification of a sensitive carboxylic acid, in particular a suitably protected amino acid, with an alcohol component, the esterification according to the invention being carried out in the presence of 2,4,6-mesitylene-1-sulfonyl-3-nitro-1,2,4-triazolide (MSNT) and a weak base in an aprotic and non-basic solvent.Type: GrantFiled: August 29, 1990Date of Patent: September 15, 1992Assignee: Gesellschaft fur Biotechnologische Forschung GmbHInventors: Birgit Blankemeyer-Menge, Ronald Frank
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Patent number: 5118837Abstract: A modified ruthenium catalyst can be used to selectively hydrogenate an olefinic double bond in the presence of another olefinic double bond in the same or in a different molecule. Modifiers are selected from compounds containing trivalent nitrogen, trivalent phosphorus and divalent sulfur.Type: GrantFiled: February 12, 1987Date of Patent: June 2, 1992Assignee: Givaudan CorporationInventors: Alan J. Chalk, Laszlo V. Wertheimer
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Patent number: 5101070Abstract: A process for preparing valproic acid which comprises:(I) producing a 2,2-dipropyl acetoacetic acid ester from an acetoacetic acid ester,(II) deacetylating the 2,2-dipropyl acetoacetic acid ester with an alcohol to give a valproic acid ester, and(III) hydrolyzing the valproic acid ester. In the process of the present invention, valproic acid can be prepared in a high yield as not less than 85% by mole and by-products such as .alpha.-propyl-.beta.-ethyl acrylic acid and its esters which cannot be easily separated from valproic acid, are not entirely produced.Type: GrantFiled: July 5, 1988Date of Patent: March 31, 1992Assignee: Nippon Gohsei Kagaku Kogyo Kabushiki KaishaInventors: Toshio Yamamoto, Akira Yamashita, Noriyoshi Numoto
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Patent number: 5087728Abstract: A process for producing a carboxylic acid or an ester thereof represented by formula (I): ##STR1## wherein: R represents a hydrogen atom or a lower alkyl group; R.sup.1 represents a lower alkyl group; CH.sub.2 COOR.sup.3, wherein R.sup.3 represents a hydrogen atom or a lower alkyl group; or NHR.sup.4, wherein R.sup.4 represents a formyl group, an acetyl group, a benzoyl group, or a chloroacetyl group, andR.sup.2 represents a hydrogen atom, a lower alkyl group, or a phenyl group,which comprises hydrogenating an unsaturated compound represented by formula (II): ##STR2## wherein R, R.sup.1, and R.sup.2 are as defined above, in the presence of a rhodium or ruthenium complex catalyst having, as a ligand, BICHEP which means 2,2'-bis(dicyclohexylphoshino)-6,6'-dimethyl-1,1'-biphenyl represented by formula (III): ##STR3## is disclosed.Type: GrantFiled: July 11, 1990Date of Patent: February 11, 1992Assignee: Takasago International CorporationInventors: Hiroyuki Nohira, Hidemasa Takaya, Akira Miyashita
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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
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Patent number: 5026904Abstract: Hydrocarbyl formates, convertible by hydrolysis into formic acid, are produced by reacting carbon dioxide and hydrogen with a compound of formula ROH wherein R is a hydrocarbyl group in the presence of a substantially insoluble compound of an element selected from Groups III to VIII of the Periodic Table, which element exhibits amphoteric or basic properties, and as catalyst a compound of a transition metal of Group VIa, VIIa or VIII of the Periodic Table, particularly rhodium, ruthenium or iridium.Type: GrantFiled: February 15, 1985Date of Patent: June 25, 1991Assignee: The British Petroleum Company p.l.c.Inventors: Philip G. Lodge, David J. H. Smith
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Patent number: 5015764Abstract: A process for the separation of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process comprises (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base (ii) treating said salt solution with one-half molar equivalent of a chiral organic nitrogenous base having a base strength no stronger than said organic or inorganic base (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt and (iv) separating said precipitated diastereomeric salt.Type: GrantFiled: June 18, 1990Date of Patent: May 14, 1991Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, Fred J. Impastato
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Patent number: 5008046Abstract: The invention is a process for the continuous liquid-phase esterification of C.sub.2 -C.sub.24 fatty acids with alkanols in countercurrent contact and reaction in a reaction column, the catalysts and fatty acids are introduced at the top plate and the alkanols below the lowest plate, at a head pressure of the reaction column of 200 to 900 hPa. The process reduces dehydration of the alkanols.Type: GrantFiled: March 21, 1989Date of Patent: April 16, 1991Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Norbert Bremus, Bernhard Gutsche, Lutz Jeromin, Eberhard Peukert, Bernard Schleper
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Patent number: 5004569Abstract: The invention relates to a process for the production of carboxylic acid esters from carboxylic acids and alcohols which is characterized in that neutral phosphites containing oxetane groups are used as esterification catalysts.Type: GrantFiled: December 6, 1988Date of Patent: April 2, 1991Assignee: Bayer AktiengesellschaftInventors: Helmut-Martin Meier, Klaus Kircher, Klaus Berg
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Patent number: 4997978Abstract: Alkyl carboxylates of the formula:R--CO--O--CH.sub.2 R'are prepared by hydrocarbonylating a compound of the formula:R--CO--O--R'in the simultaneous presence, in the reaction medium, of cobalt, ruthenium, an alkyl iodide and an ionic iodide, the atomic ratio Co/Ru being less than or equal to 1, and the total amount of iodine-containing promoters present in the medium being such that I/Ru is greater than or equal to 5.Type: GrantFiled: October 24, 1988Date of Patent: March 5, 1991Assignee: Rhone-Poulenc IndustriesInventors: Jean Gauthier-Lafaye, Robert Perron
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Patent number: 4996357Abstract: Acetic acid is advantageously prepared from a starting material having a formic acid moiety and a methyl ester moiety by heating said starting material in the presence of (1) carbon monoxide, (2) at least one of (2-a) a metal accelerator selected from beryllium, a metal belonging to the group IIIA, IVB, VB, VIB or IIA of the Periodic Table, a lanthanide metal and an actinide metal and (2-b) an onium compound or a precursor for the onium compound, (3) a rhodium catalyst and (4) an iodine compound.Type: GrantFiled: March 29, 1985Date of Patent: February 26, 1991Assignee: Daicel Chemical Industries, Ltd.Inventors: Hidetaka Kojima, Takaaki Fujiwa
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Patent number: 4990651Abstract: Carboxylic acid esters, industrially important compounds, are obtained by reacting carboxylic acid amides and formic acid esters, or carboxylic acid amides, alcohols and carbon monoxide in the presence of metal alcoholate.Type: GrantFiled: April 12, 1989Date of Patent: February 5, 1991Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hideo Ikarashi, Yoshio Kawai, Seiji Nagasawa, Hiroyuki Hirayama
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Patent number: 4990458Abstract: A process for forming derivatives of organic compounds as a step during their analysis. A macroreticular resin is used as both an adsorbent for the analyte and the derivatizing reagent and also as a catalyst for the derivatization reaction. Subsequent serial elution of the absorbed compounds leads to simple separation of the derivatized analyte from the starting materials. Further, the resin impregnated with derivatizing reagent can be used to combine the extraction and derivatization of the analyte. As macroreticular resins are relatively inexpensive, they result in reduced costs compared with conventional catalysts, and their ease of separation from liquid systems makes them easy to use and makes it possible to automate the procedure.Type: GrantFiled: September 22, 1987Date of Patent: February 5, 1991Assignee: McMaster UniversityInventor: Jack M. Rosenfeld
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Patent number: 4985572Abstract: An alcohol and/or a carboxylic acid ester is produced from a carboxylic acid or anhydride thereof by reacting the acid or anhyride with hydrogen at elevated temperature in the presence as catalyst of a composition comprising an alloy of (i) at least one noble metal of Group VIII of the Periodic Table and (ii) at least one metal capable of alloying with the Group VIII noble metal, optionally including a support and at least one of the metals rhenium, tungsten or molybdenum. The process is particularly applicable to the hydrogenation of monobasic acids, for example acetic acid, and the hydrogenation of maleic acid or maleic anhydride to gamma-butyrolactone.Type: GrantFiled: November 21, 1988Date of Patent: January 15, 1991Assignees: The British Petroleum Company, p.l.c., BP Chemicals LimitedInventors: Melanie Kitson, Peter S. Williams
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Patent number: 4983757Abstract: Carboxylic acid esters and formamide are efficiently obtained for reacting carboxylic acid amides and formic acid esters, or carboxylic acid amides, alcohols and carbon monoxide in the presence of an alkaline earth metal oxide catalyst.Type: GrantFiled: March 28, 1990Date of Patent: January 8, 1991Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Jiro Ishikawa, Hirofumi Higuchi, Shuji Ebata, Koichi Kida
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Patent number: 4978778Abstract: A process for producing vinyl acetate which comprises reacting acetic anhydride with hydrogen in the presence of a catalyst comprising(a) a metal belonging to Group VIII of the Periodic Table or a compound of the metal, and(b) (i) an acidic substance, or (ii) a halideis disclosed.Type: GrantFiled: December 13, 1983Date of Patent: December 18, 1990Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomiya Isshiki, Yasuhiko Kijima, Akiro Ito, Yuh Miyauchi, Takao Konko, Takayuki Watanabe
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Patent number: 4973713Abstract: A process for the production of esters or lactones, comprising reacting in the presence of a catalyst and under hydrogenation conditions hydrogen and an acyclic or cyclic carboxylic anhydride to produce the corresponding ester or lactone, wherein the catalyst is a supported catalyst comprising:(a) a group VIII metal, Re and Fe;(b) a group VIII metal on TiO.sub.2 ;(c) Ru and at least one of Re, Ag or Cu; or(d) Pd and Fe.Preferably, the anhydride has the formula ##STR1## and is reacted to form an ester of the formula ##STR2## or a lactone of the formula ##STR3## wherein R and R.sup.1 independently are lower alkyl or cycloalkyl; R.sup.2, R.sup.3, R.sup.4, R.sup.5 independently are hydrogen, lower alkyl, cycloalkyl or aryl; and wherein R.sup.3 and R.sup.4 taken together may form a saturated or unsaturated ring, or an aromatic ring. The more preferred starting material is phthalic anhydride.Type: GrantFiled: November 28, 1989Date of Patent: November 27, 1990Assignee: E. I. du Pont de Nemours and CompanyInventor: William H. Manogue
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Patent number: 4973739Abstract: Carboxylic acid esters, industrially important compounds, are efficiently obtained by reacting carboxylic acid amides with formic acid esters in the presence of an inorganic solid acid catalyst.Type: GrantFiled: April 12, 1989Date of Patent: November 27, 1990Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Seiji Nagasawa, Hideo Ikarashi, Yoshio Kawai, Hiroyuki Hirayama
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Patent number: 4970069Abstract: According to the present invention, an attractant that possesses attraction effects with respect to Tribolium castaneum Herbst and moreover, is a stable compound for which the effectiveness will be continuous, is provided.That is, the present invention is 2,6-dimethyl octylformate and an atrractant of Tribolium castaneum Herbst which is formed from relevant chemical compounds.Type: GrantFiled: March 23, 1989Date of Patent: November 13, 1990Assignee: Japan Tobacco, Inc.Inventors: Masahiro Kono, Tatsuji Chuman, Takane Fujimori, Kenji Mori, Shigefumi Kuwahara
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Patent number: 4960952Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more lanthanum compounds comprising silicate, metasilicate and mixtures thereof. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: August 31, 1989Date of Patent: October 2, 1990Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 4957648Abstract: A spin fiber lubricant composition is disclosed. The composition is essentially comprised of a liquid carrier having therein an ester of the general structural formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are hydrocarbyl groups preferably in the form of alkyl groups containing 1-6 carbon atoms. The composition has been found to be useful in connection with providing materials with lubricating properties which are desirable for the spinning of fibers.Type: GrantFiled: February 7, 1990Date of Patent: September 18, 1990Assignee: The Lubrizol CorporationInventors: Richard Yodice, Gregory A. Lentz
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Patent number: 4939294Abstract: In a process for the production of methyl acetate from methanol and glacial acetic acid involving countercurrently flowing acetic acid and methanol through a single reactive distillation column having an extractive distillation section and a methyl acetate/acetic acid rectification section to obtain methyl acetate in the presence of an acidic catalyst, the improvement which comprises producing ultra high purity methyl acetate by the additional step of introducing acetic anhydride and a salt-free acid catalyst into the reactive distillation column between the extractive distillation section and the methyl acetate/acetic acid rectification section.Type: GrantFiled: May 22, 1989Date of Patent: July 3, 1990Assignee: Eastman Kodak CompanyInventors: Victor H. Agreda, Ronnie D. Lilly
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Patent number: 4927967Abstract: A process for the production of organic carboxylic acids by the catalytic reaction of organic formate esters in contact with carbon monoxide and a homogeneous catalyst system of rhodium metal atom, a phosphorus containing ligand in which there is present at least one oxo oxygen atom attached to a phosphorus atom or a carbon atom to form a Z group and the ##STR1## group in said Z group is located at least one carbon atom removed and preferably from 2-4 carbon atoms removed from the phosphorus atom of the molecules represented by the formulas ##STR2## and a halogen source, under mild reaction conditions, wherein R' is H, aryl, alkaryl, aralkyl or alkyl, and wherein 1 or more of said R' groups can be substituted with a Z group but not more than 3 of said R' groups in the molecule are so substituted; a is an integer from 0-4; b is an integer from 0-3; and Z is P(O)R'R'; --C(O)OR" or C(O)R", wherein R" is R'.Type: GrantFiled: November 6, 1985Date of Patent: May 22, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: Richard W. Wegman
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Patent number: 4910321Abstract: This invention provides a novel catalyst composed of a complex of an organic acid or its ester and a Lewis acid, preferably boron trichloride that can add olefin monomers to increase the molecular weight of the complex from as low as 200 to in excess of a million, with the complex being active viz., living, until the complex dies, viz., is decomposed or destroyed so that polymers in the liquid or easily liquefiable range of 300 to about 20,000 can be made or those more difficult to be liquefied or unliquefiable, viz., those of over 10,000 up to 100,000 or in some cases 500,000 and then those in the range of the elastomers, or moldable or extrudable plastics range having very high molecular weights, generally in excess of 100,000 up to in excess of 500,000 and having useful end groups such as the halogens and specifically chloride, allyl, acryl or methacryl, acetate or formate to name some of the more useful ones.Type: GrantFiled: February 16, 1988Date of Patent: March 20, 1990Assignee: University of AkronInventors: Joseph P. Kennedy, Rudolf Faust
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Patent number: 4897473Abstract: This invention produces higher homologs, i.e., differing by at least a --CH.sub.2 -unit, of carbonyloxy-containing compounds by treating the carbonyloxy-containing compounds with carbon monoxide and hydrogen in the presence of a ruthenium-containing compound, a proton donor, an iodide promoter, and optionally, a manganese-containing compound.Type: GrantFiled: May 1, 1981Date of Patent: January 30, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: Bernard D. Dombek
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Patent number: 4886905Abstract: Process for the preparation of ethylidene diacetate and/or ethyl acetate by hydrogenating acetic anhydride in the presence of a homogeneous ruthenium catalyst, methyl iodide and, optionally, lithium iodide. The process can also be utilized to hydrogenate mixtures of acetic anhydride and ethylidene diacetate to produce ethyl acetate.Type: GrantFiled: May 23, 1983Date of Patent: December 12, 1989Assignee: Eastman Kodak CompanyInventor: Thomas H. Larkins, Jr.