Polycarboxylic Acid Patents (Class 560/176)
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Patent number: 5997610Abstract: The invention concerns amphiphilic compounds of general formula (I) ##STR1## with at least two hydrophilic and at least two hydrophobic groups based on diacarboxylic acid diamides. The amphiphilic compounds according to the invention are mostly surface-active and are suitable for use as emulsifiers, demulsifiers, detergents, dispergents and hydrotropic agents in industry and households, for example, in the treatment of metals, ore processing, surface finishing, washing, cleaning, cosmetics, medicine and food processing and preparation.Type: GrantFiled: August 18, 1997Date of Patent: December 7, 1999Assignee: Huels AktiengesellschaftInventors: Klaus Kwetkat, Wulf Ruback
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Patent number: 5932761Abstract: It is provided a process for industrially advantageously producing a branched aldehyde represented by the formula; ##STR1## ?wherein Y represents an acyl group of two or more carbon atoms; and X represents an acyloxymethyl group represented by --CH.sub.2 OY' (where Y' represents an acyl group of two or more carbon atoms), cyano group or an alkoxycarbonyl group! which is useful as an intermediate for pharmaceuticals and agricultural chemicals, comprising subjecting an olefinic compound represented by the following formula; ##STR2## (wherein Y and X are the same as defined above), to the reaction with hydrogen and carbon monoxide in the presence of a rhodium compound and a tertiary organic phosphorus compound with an electronic parameter (.upsilon.-value) of 2080 to 2090 cm.sup.-1 or with a steric parameter (.theta.-value) of 150 to 180.degree..Type: GrantFiled: March 23, 1998Date of Patent: August 3, 1999Assignee: Kuraray Co., Ltd.Inventors: Toshihiro Omatsu, Masahiko Kitayama, Takashi Onishi
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Patent number: 5837782Abstract: A novel bis(mono- or diperoxyoxalate) composition of Structure A, ##STR1## and use of the novel bis(mono- or diperoxyoxalate) composition as an initiators for curing of unsaturated polyester resins and for polymerizing ethylenically unsaturated monomers are disclosed.Type: GrantFiled: October 10, 1997Date of Patent: November 17, 1998Assignee: Elf Atochem North America, Inc.Inventor: Jose Sanchez
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Patent number: 5767292Abstract: The present invention relates to processes for preparing 1-methoxy-2-propyl 3-(7-diethylamino-2-oxo-2H-chromen-3-yl)-3-oxopropionate of the formula I ##STR1## and also di(1-methoxy-2-propyl) acetonedicarboxylate as intermediate for one of the processes.Type: GrantFiled: May 22, 1997Date of Patent: June 16, 1998Assignee: Hoechst AktiengesellschaftInventors: Peter Koch, Wolfgang Bauer
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Patent number: 5736274Abstract: A polymer containing a recurring unit of a conjugated N-fluoropyridinium salt and an active material for a positive electrode, an electrolyte, a battery material for the positive electrode and a battery which use such a polymer. That polymer provides a battery material and a primary battery or a secondary battery which have high electromotive force, high energy density, high environmental acceptability, a low internal resistance in charging and discharging and strong recoverability of the electromotive force, and can be useful as a fluorinating agent.Type: GrantFiled: April 18, 1997Date of Patent: April 7, 1998Assignee: Daikin Industries, Ltd.Inventors: Teruo Umemoto, Kenji Adachi, Ginjiro Tomizawa, Sumi Ishihara, Masayuki Nagayoshi
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Patent number: 5679830Abstract: A pivaloylacetic acid ester is prepared at a high yield by decarbonylating a pivaloylpyruvic acid ester in gas or liquid phase in the presence of an inorganic oxide catalyst which comprises aluminum in an amount of 10% by weight or more in terms of aluminum oxide, and preferably is substantially free from heavy metals, for example, Fe, Cu, Ni, Mn, Cr, Mo and Co, and exhibits a high catalytic activity and chemical stability.Type: GrantFiled: July 12, 1995Date of Patent: October 21, 1997Assignee: Ube Industries, Ltd.Inventors: Katsuhiko Mizutare, Masayoshi Oku, Tsuyoshi Ueyama
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Patent number: 5667901Abstract: Provided are various 2-acetylglutarate esters of polyols which are useful as poller crosslinkers for use in thermosetting coating compositions, as well as methods of preparation of these materials. In particular, the invention provides crosslinkers of the formula ##STR1## wherein R and R' are independently t-butyl, t-amyl, or phenyl, and x is an integer of from 2 to 5.Type: GrantFiled: February 20, 1996Date of Patent: September 16, 1997Assignee: Eastman Chemical CompanyInventors: Philip C. Heidt, Charles H. Foster, J. Stewart Witzeman
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Patent number: 5527950Abstract: The invention relates to a process for the preparation of a 5-formylvalerate ester by hydroformylating a mixture of pentenoate esters in the presence of a catalyst system which catalyst system comprises a metal from group 8-10 of the Periodic Table of Elements and a mono- or multidentate organic phosphorous ligand, wherein the mixture of pentenoate esters contains less than 500 ppm hydroperoxide compounds.Type: GrantFiled: December 28, 1994Date of Patent: June 18, 1996Assignees: DSM N.V., E.I. Du Pont de Nemours & Co.Inventors: Carolina B. Hansen, Antonius J. J. M. Teunissen
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Patent number: 5466863Abstract: Provided are 3-oxoadipate esters of certain polyols which are useful as crosslinkers in thermosetting coating compositions. Also provided are such thermosetting compositions comprised of a curable hydroxyl-functional polymer such as a polyester or acrylic and the crosslinkers of the present invention. Such compositions offer a significant improvement in curing temperature.Type: GrantFiled: February 6, 1995Date of Patent: November 14, 1995Assignee: Eastman Chemical CompanyInventors: Philip C. Heidt, Charles H. Foster, J. Stewart Witzeman, Allen L. Crain
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Patent number: 5412151Abstract: Provided are 3-oxoadipate esters of certain polyols which are useful as crosslinkers in thermosetting coating compositions. Also provided are such thermosetting compositions comprised of a curable hydroxyl-functional polymer such as a polyester or acrylic and the crosslinkers of the present invention. Such compositions offer a significant improvement in curing temperature.Type: GrantFiled: October 22, 1993Date of Patent: May 2, 1995Assignee: Eastman Chemical CompanyInventors: Philip C. Heidt, Charles H. Foster, J. Stewart Witzeman, Allen L. Crain
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Patent number: 5359125Abstract: Disclosed are certain novel 2,2'-bisacetoacetates useful as crosslinking agents and a process for the preparation therefor. Also provided are novel enamel compositions containing the crosslinkers and coatings and articles coated with thermosetting coating compositions crosslinked with these novel crosslinkers.Type: GrantFiled: August 9, 1993Date of Patent: October 25, 1994Assignee: Eastman Chemical CompanyInventors: J. Stewart Witzeman, Allen L. Crain
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Patent number: 5260424Abstract: Silylketene acetals, including "living" GTP polymers, are acylated or sulfonylated in the presence of GTP-effective catalysts with acyl or sulfonyl compounds to produce .beta.-ketoesters or .beta.-sulfonylesters; polymeric products, including capped, coupled and chain-extended polymers and block copolymers can be prepared.Type: GrantFiled: February 3, 1992Date of Patent: November 9, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Gordon M. Cohen, Hans J. Reich
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Patent number: 5260465Abstract: This invention relates to pharmaceutical compounds of structural formula (I): ##STR1## and compositions and methods of treatment utilizing these compounds to inhibit farnesyl protein transferase and farnesylation of the oncogene protein Ras.Type: GrantFiled: December 16, 1991Date of Patent: November 9, 1993Assignee: Merck & Co., Inc.Inventors: Sheo B. Singh, Deborah L. Zink
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Patent number: 5247122Abstract: Disclosed are certain novel 2,2'-bisacetoacetates useful as crosslinking agents and a process for the preparation therefor. Also provided are novel enamel compositions containing the crosslinkers and coatings and articles coated with thermosetting coating compositions crosslinked with these novel crosslinkers.Type: GrantFiled: June 3, 1991Date of Patent: September 21, 1993Assignee: Eastman Kodak CompanyInventors: J. Stewart Witzeman, Allen L. Crain, Robert J. Clemens
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Patent number: 5223621Abstract: Transvinylation process between vinyl acetate or vinyl propionate and a carboxylic acid of general formula (I),RCOOH (I)in which R represents a substituted or non-substituted alkyl, cycloalkyl, aralkyl or aromatic radical, in the presence of a palladium catalyst, in which the catalyst is obtained in situ, by reacting, in the reaction medium, a derivative of palladium chosen from the group constituted by palladium II acetate, nitrate or hydroxide and palladium deposited on charcoal, with a tertiary amine chosen from the group constituted by 2,2'-bipyridyl, orthophenanthroline or tetramethylethylenediamine, that the quantity of palladium used, expressed in gram-atom of palladium II per 100 moles of carboxylic acid of general formula (I) is between 0.005 and 1 and that the quantity of amine is greater than 1 and less than 10 moles per gram-atom of palladium II used and use for the preparation of certain products.Type: GrantFiled: January 6, 1992Date of Patent: June 29, 1993Assignee: Societe Francaise HoechstInventors: Jean-Claude Vallejos, Yani Christidis
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Patent number: 5214197Abstract: A novel 2,4-dihydroxyadipic acid derivative of the formula: ##STR1## wherein R.sup.1 and R.sup.4 are the same or different and each a hydrogen atom, an alkyl group, an aralkyl group, an aryl group or a silyl group, and R.sup.2 and R.sup.3 are the same or different and each a hydrogen atom or a protective group of a hydroxy group or together form a ring, which is useful as a common intermediate in the synthesis of HMG-CoA reductase inhibitor.Type: GrantFiled: July 2, 1991Date of Patent: May 25, 1993Assignee: Kanegafuchi Chemical Industry Co., Ltd.Inventors: Shigeo Hayashi, Noboru Ueyama, Kenji Inoue, Teruyoshi Koga, Satomi Takahashi
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Patent number: 5210222Abstract: A process, which is harmless with respect to safety, for the production of malonic acid anhydride. For this purpose, diketene is ozonized in the presence of a suitable carbonyl compound. Malonic acid anhydride is a highly reactive intermediate product for the synthesis of numerous active ingredients for, e.g., pharmaceutical agents, pesticides or dyes.Type: GrantFiled: January 21, 1992Date of Patent: May 11, 1993Assignee: Lonza Ltd.Inventor: Colm O'Murchu
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Patent number: 5206419Abstract: Process for the preparation of acetoacetates and other .beta.ketoesters is provided, involving reaction of nitrogen, oxygen or sulfur nucleophiles with a tertiaryalkyl acetoacetate or tertiaryalkyl .beta.-ketoester.Type: GrantFiled: February 25, 1992Date of Patent: April 27, 1993Assignee: Eastman Kodak CompanyInventors: J. Stewart Witzeman, W. Dell Nottingham
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Patent number: 5175300Abstract: A process for preparing pyridine-2,3-dicarboxylic acid compounds of the following formula, which comprises preparing .alpha.-halo-oxalacetic acid diesters by reacting oxalacetic acid diester alkali metallic salts with an acid and a halogenating agent or by reacting oxalic acid diesters with halo-acetic acid esters, and then reacting the obtained .alpha.-halo-oxalacetic acid diesters with 2-propenal compounds and ammonia. ##STR1## wherein R.sup.1 and R.sup.2 are, identical or different, a lower alkyl group, and R.sup.3 is a hydrogen atom or a lower alkyl group.The pyridine-2,3-dicarboxylic acid componds obtained by the process of the ivention are useful as an intermediate for manufacturing agricultural chemicals and pharmaceuticals.Type: GrantFiled: January 9, 1991Date of Patent: December 29, 1992Assignee: Sugai Chemical Ind. Co., Ltd.Inventors: Takaharu Yamashita, Mitsuhiro Kodama
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Patent number: 5169979Abstract: The invention relates to a curing component (A) containing active CH groups, which contains at least two groups of the formula (I) ##STR1## or structural units of the formula (I') or (I") ##STR2## in which: A denotes ##STR3## X and Y are identical or different and denote ##STR4## CO.sub.2 R.sup.1, CN, NO.sub.2, CONH.sub.2, CONR.sup.1 H or CONR.sup.1 R.sup.1, where the R.sup.1 radicals may be identical or different and represent a hydrocarbon radical, preferably an alkyl radical having 1 to 12 carbon atoms, which may also be interrupted by oxygen or an N-alkyl radical, with the proviso that only one of the two radicals X and Y may represent the NO.sub.2 group;A' denotes ##STR5## X' and Y' are identical or different and denote ##STR6## Curable mixtures of (A) and a Michael acceptor (B) and, if appropriate diluents and customary additivies cure rapidly even at low temperatures and are suitable, in particular for surface-coating preparations.Type: GrantFiled: November 30, 1990Date of Patent: December 8, 1992Assignee: Hoechst AGInventors: Uwe Kubillus, Gerhard Brindopke, Helmut Plum
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Patent number: 5107015Abstract: The preparation of 2-formyl-2-methyl succinates by reacting itaconates with carbon monoxide and hydrogen in contact with a catalyst system comprising rhodium and a tertiary phosphorus compound, wherein the reaction is carried out under a pressure of from 90 to 325 bar.Type: GrantFiled: October 24, 1990Date of Patent: April 21, 1992Assignee: BASF AktiengesellschaftInventors: Werner Bertleff, Gerhard Butz
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Patent number: 4981973Abstract: A process for the transvinylation of a vinyl derivative of a Bronsted acid with a different Bronsted acid which comprises providing a liquid phase mixture containing said vinyl derivative and said Bronsted acid in the presence of a ruthenium compound at a temperature at which transvinylation occurs and recovering as a product of transvinylation the vinyl derivative of the different Bronsted acid. The process is most favorably employed using carboxylic acids to make vinyl esters of carboxylic acids.Type: GrantFiled: June 30, 1988Date of Patent: January 1, 1991Assignee: Union Carbide Chemicals and Plastics Company, Inc.Inventor: Rex E. Murray
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Patent number: 4902820Abstract: Disclosed is a process for the preparation of .alpha.-acyloxycarbonyl compounds by contacting the corresponding .alpha.-dicarbonyl compound with an acyl iodide, which can be employed in an essentially pure form or generated in solution from hydrogen iodide and a carboxylic acid anhydride.Type: GrantFiled: February 21, 1989Date of Patent: February 20, 1990Assignee: Eastman Kodak CompanyInventor: Joseph R. Zoeller
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Patent number: 4849542Abstract: A process for the preparation of oxo-alkanedioic acids or diesters thereof by reacting an alkenoic acid or an ester thereof, at least one of the C atoms of the carbon carbon double bond carrying a H atom, with CO and H.sub.2 in the presence of a catalytic system prepared by combining:a. Pd and/or a Pd compound,b. a compound containing an anion of an acid having a pKa of less than 2, except hydrohalogenic acid and carboxylic acids, andc. a bidentate ligandR.sup.1 R.sup.2 --M--R--M--R.sup.3 R.sup.4wherein M is P, As or Sb, R is a divalent organic bridging group having at least two C atoms in the bridge, and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are optionally substituted hydrocarbon groups.Type: GrantFiled: October 28, 1986Date of Patent: July 18, 1989Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4800231Abstract: Novel keto-diesters are produced by a 2:1 condensation of lower alkyl esters of .alpha.,.beta.-ethylenically unsaturated carboxylic acids and aldehydes having two hydrogen atoms as portions of a formyl group, in the presence of a thiazolium salt as catalyst and a tertiary amine.Type: GrantFiled: March 23, 1988Date of Patent: January 24, 1989Assignee: Shell Oil CompanyInventor: Pen C. Wang
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Patent number: 4644036Abstract: Michael addition products of monocarboxylic or dicarboxylic acid esters, capable of undergoing Michael addition, with compounds containing double bonds capable of undergoing Michael addition are suitable for use as a curing component for synthetic resins containing groups capable of amide formation and/or ester formation with carboxylic acids. In particular, the Michael addition products of acetoacetic esters or malonic esters with esters, amides or urea derivatives of .alpha., .beta.-unsaturated monocarboxylic or dicarboxylic acids are used. The structure and the functionality of the curing component can be varied in many ways. It can be attached directly to the synthetic resin molecule, so that self-curing synthetic resins are obtained.Type: GrantFiled: April 26, 1984Date of Patent: February 17, 1987Assignee: Hoechst AktiengesellschaftInventors: Gerd Walz, Ernst-August Theiling
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Patent number: 4600781Abstract: The invention relates to 2-formyl-2-halomalonates, and their preparation. The compounds are useful in the preparation of their acetals and also in the preparation of 2-(dicarbethoxymethylene)thiazolidine-4-carboxylic acid.Type: GrantFiled: July 2, 1984Date of Patent: July 15, 1986Assignee: The United States of America as represented by the Secretary of AgricultureInventor: Ivan A. Wolff
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Patent number: 4584145Abstract: There is described a process for preparing carbonyl compounds of formula: ##STR1## by oxidation of compounds of formula: ##STR2## wherein X=--CN, --COOR, Y=--COOR.sub.1, --CN, and R, R.sub.1, like or unlike each other, are inert radicals, by employing oxygen or air as oxidants, at least a catalyst selected from the salts of organic or inorganic acids of Mn, Co, Cu and Fe, from 0 to 60 moles of an alkaline salt of an aliphatic carboxylic acid per gram-atom of catalyst metal, in a polar solvent, at temperatures ranging from 30.degree. C. to 200.degree. C. and maintaining the reaction medium anhydrous.The present invention relates to a process for preparing carbonyl compounds by catalytic oxidation of compounds containing an activated methylene group.Type: GrantFiled: June 19, 1985Date of Patent: April 22, 1986Assignee: Montedison S.p.A.Inventors: Roberto Santi, Giuseppe Cometti, Anselmo Pagani
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Patent number: 4578503Abstract: An alkylated or alkenylated malonic ester having a fluorine containing aliphatic substituent and derivatives thereof as expressed by the following general formula: ##STR1## where R.sub.f is a fluorine containing aliphatic group, R is an aliphatic group, or hydrogen or alkali metal atom, and R' is an unsubstituted or substituted aliphatic group.And a method to trap the enolate ion of a malonic ester having a fluorine containing aliphatic substituent as expressed by the following general formula,R.sub.f CH(CO.sub.2 R).sub.2where R.sub.f is a fluorine containing aliphatic group and R is an aliphatic group, hydrogen or alkali metal atom, wherein said malonic ester is converted under the action of a weaker base and/or fluoride ion to a fluorine containing enolate ion to be trapped as expressed by the following general formula:R.sub.f C.sup..crclbar. (CO.sub.2 R).sub.2where R.sub.f and R are the same as above.Type: GrantFiled: August 31, 1983Date of Patent: March 25, 1986Assignee: Daikin Kogyo Co., Ltd.Inventors: Nobuo Ishikawa, Takeshi Nakai, Yoshio Inouye
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Patent number: 4518793Abstract: Disclosed is a process for preparing an acetone dicarboxylic acid diester, which comprises allowing diketene, carbon monoxide and a nitrous acid ester to react in the presence of a palladium halide or a complex thereof.Type: GrantFiled: October 17, 1983Date of Patent: May 21, 1985Assignee: UBE Industries, Ltd.Inventors: Shinichiro Uchiumi, Kikuo Ataka
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Patent number: 4401827Abstract: Novel acyl-derivatives of the .beta.-hydroxy-.gamma.-butyrobetaine are disclosed (typically pyruvyl carnitine hydrochloride) which are useful therapeutic agents in the treatment of cardiac disorders, hyperlipidoemias and hyperlipoproteinemias.Type: GrantFiled: December 28, 1981Date of Patent: August 30, 1983Assignee: Sigma-TauInventor: Paolo de Witt
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Patent number: 4343953Abstract: The present invention relates to a novel method for producing cyclopentenolone of the formula (I), ##STR1## which is a useful intermediate for producing agricultural chemicals, which comprises reacting an acetonedicarboxylic ester of the formula (VII), ##STR2## wherein R is a C.sub.1 -C.sub.6 alkyl group, with 2-propynyl chloride in the presence of magnesium alkoxide and in the presence of alkali iodide to obtain novel mono-(2-propynyl)-substituted acetonedicarboxylic ester of the formula (VI), ##STR3## wherein R is as defined above; hydrolyzing the mono-(2-propynyl)-substituted acetonedicarboxylic ester of the formula (VI) under alkaline conditions with an alkali and then reacting the hydrolyzed product with methylglyoxal of the formula, ##STR4## to obtain novel .gamma.-diketone of the formula (V), ##STR5## and ring-closing the .gamma.-diketone of the formula (V) under alkaline condition.Type: GrantFiled: June 16, 1980Date of Patent: August 10, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Noritada Matsuo, Nobushige Itaya, Kohichi Aketa, Osamu Magara, Toshio Nishioka
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Patent number: 4338459Abstract: A diester of .alpha.-acetyl-.alpha.'-methylsuccinic acid is prepared in improved yield under substantially anhydrous process conditions which minimizes decomposition of that diester by reacting an acetoacetate ester with an .alpha.-halopropionate ester in a solvent mixture containing a non-polar, aprotic liquid, e.g., toluene, and a dipolar aprotic liquid, e.g., DMF, at from about 50.degree. C. to reflux temperature in the presence of a phase transfer agent, a catalytic amount of iodide ion and solid form, substantially anhydrous alkali metal base or basic salt. Further improvement is obtained when the completed reaction mixture is diluted with water and adjusted to pH 8 to 9, and when the DMF/acetoacetate ester ratios are between about 1.7 and 3. The resulting diesters can be used under the conditions of this invention as intermediates in processes for making ibuprofen by combining and reacting the .alpha.-acetyl-.alpha.Type: GrantFiled: March 5, 1981Date of Patent: July 6, 1982Assignee: The Upjohn CompanyInventor: Francis L. Shenton
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Patent number: 4324906Abstract: A process is disclosed for converting a compound of the formula ##STR1## wherein R and R" are independently methyl, ethyl or propyl;R' is H, Na, Li, K, Mg.sub.1/2, Ca.sub.1/2, Sr.sub.1/2, Ba.sub.1/2, methyl, ethyl or propyl; andQ is chlorine or bromide;directly to a citrate salt by heating in an aqueous medium, with an alkaline earth metal hydroxide, at a temperature greater than 160.degree. C.Type: GrantFiled: August 20, 1979Date of Patent: April 13, 1982Assignee: Lever Brothers CompanyInventors: Eddie N. Gutierrez, Vincent Lamberti
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Patent number: 4311706Abstract: Novel, transient prodrug forms of dopa and dopamine have (i) the structural formula (I): ##STR1## wherein each R is independently selected from the group consisting of hydrogen, R.sup.3 -CO- and ##STR2## wherein X is O, S or NR.sup.6 ; R.sup.1 is hydrogen or --COOR.sup.8 ; R.sup.2 is hydrogen or OR; R.sup.Type: GrantFiled: January 22, 1980Date of Patent: January 19, 1982Assignee: INTERx Research CorporationInventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4306079Abstract: Novel polyfunctional compounds and a novel process for their preparation are disclosed. These compounds may be converted into the acid or salt forms of cis and trans aconitic acids as well as into a racemic mixture of isocitric acid, alloisocitric acid and the lactones of isocitric acid and alloisocitric acid and their salts. All of the acid and salt forms produced are useful as metal sequestrants and/or detergent builders. The novel polyfunctional compounds can also be saponified to their corresponding alkali metal salts which, in turn, are also metal ion sequestering agents and detergent builders. The polyfunctional compounds are the reaction products obtained from the reaction of selected salts of monoalkyl esters of maleic acid with selected active hydrogen containing compounds.Type: GrantFiled: September 12, 1979Date of Patent: December 15, 1981Assignee: Lever Brothers CompanyInventors: Eddie N. Gutierrez, Vincent Lamberti
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Patent number: 4304927Abstract: Compounds of the structure ##STR1## wherein X is --F or Cl and each R is independently --H, --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 CH.sub.3, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 or M where M is an alkali metal, an alkaline earth metal, ammonium or a quaternary ammonium are disclosed. The above compounds are prepared by treating a compound of the structure ##STR2## where each R.sup.1 is independently --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 CH.sub.3 or --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 ; or ##STR3## with a strong protic acid, followed, as desired, by base hydrolysis to form carboxylate salts (R.dbd.M).Type: GrantFiled: November 11, 1977Date of Patent: December 8, 1981Assignee: E. I. DuPont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 4301186Abstract: This invention relates to new ammonium salts of .alpha.-ketocarboxylic acids, to their use for the production of amines in situ by photochemical decomposition and to photochemically hardenable coating compositions containing these ammonium salts.Type: GrantFiled: June 28, 1979Date of Patent: November 17, 1981Assignee: Bayer AktiengesellschaftInventors: Wolfram Mayer, Hans Rudolph, Eckhard De Cleur, Manfred Schonfelder
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Patent number: 4283553Abstract: Disclosed are novel hydroperoxide derivatives of hydroxyethylated compounds of the general formula: ##STR1## a-whole number 10 to 30, b, c are absent, R=n-alkyl from C.sub.8 to C.sub.20, secondary alkyl of C.sub.14, C.sub.15 and ##STR2## where R.sub.2 =n-alkyl from C.sub.8 to C.sub.12 ##STR3## where R.sub.3 and R.sub.4 =R.sub.8 --C.dbd.O, where R.sub.8 =--CH.sub.3 or H, if R.sub.6,7,9 =H R.sub.5 is absent or ##STR4## where R.sub.9 =--CH.sub.3 or H, if R.sub.6,7,8 =H, R.sub.5 is absent; R.sub.10 =n-alkyl of C.sub.1 to C.sub.9 of R.sub.3 .noteq.R.sub.4 R.sub.5 =--CH.sub.2 if R.sub.6,7,8,9 =H; if R.sub.5 is absent, R.sub.1 is acyclic and is ##STR5## R.sub.6 =--CH.sub.3 or H, if R.sub.7,8,9 =H, R.sub.5 is absent, R.sub.7 =--CH.sub.3 or H, if R.sub.6,8,9 =H, R.sub.5 is absent, with x=--O--, b-whole number of 8 to 24, (a+c)-whole number of 6 to 30R=R.sub.Type: GrantFiled: September 24, 1979Date of Patent: August 11, 1981Inventors: Sergei S. Ivanchev, Anatoly A. Syrov, Valery N. Pavljuchenko, Ninel N. Lesnikova, Diana A. Rozhkova
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Patent number: 4272442Abstract: Novel polyfunctional compounds and a process for their preparation are disclosed. These compounds and their alkali metal salts are useful metal sequestrants and/or detergent builders. Selected compounds are also intermediates useful in the syntheses of aconitic acid as well as isocitric and alloisocitric acids and their lactones. The novel polyfunctional compounds are obtained from the reaction of maleic anhydride with selected active methylene or methine containing compounds.Type: GrantFiled: December 17, 1979Date of Patent: June 9, 1981Assignee: Lever Brothers CompanyInventor: Eddie N. Gutierrez
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Patent number: 4259518Abstract: The invention concerns new 3-methyl-5-keto-.alpha.,.omega.-alkene-dioic acids of the general formula ##STR1## wherein the double bond is in one of the positions indicated by the broken lines,R.sub.1 and R.sub.2 independently of one another are a hydrogen atom or a C.sub.1 -C.sub.4 -alkyl group,x is an integer from 9 to 11 andy and z independently of one another are 1 or 2, but cannot both be 1;a process for their preparation and their use for the preparation of macrocyclic .beta.-methyl ketones which are valuable fragrances.Type: GrantFiled: August 30, 1979Date of Patent: March 31, 1981Assignee: Bayer AktiengesellschaftInventors: Kurt Bauer, Detlef Hagena
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Patent number: 4220799Abstract: The known condensation reaction of lower alkanoylacetic acid lower alkyl esters with aldehydes catalyzed by amines proceeds safe and in high yields if the amineis an aliphatic tertiary amine. The products are precursors of aromatic amines.Type: GrantFiled: December 1, 1977Date of Patent: September 2, 1980Assignee: Hoechst AktiengesellschaftInventors: Rudiger Berthold, Bernhard Mees, Hartmut Heise
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Patent number: 4209636Abstract: Novel polyfunctional compounds and a novel process for their preparation are disclosed. These compounds may be converted into the acid or salt forms of cis and trans aconitic acids as well as into a racemic mixture of isocitric acid, alloisocitric acid and the lactones of isocitric acid and alloisocitric acid and their salts. All of the acid and salt forms produced are useful as metal sequestrants and/or detergent builders. The novel polyfunctional compounds can also be saponified to their corresponding alkali metal salts which, in turn, are also metal ion sequestering agents and detergent builders. The polyfunctional compounds are the reaction products obtained from the reaction of selected salts of monoalkyl esters of maleic acid with selected active hydrogen containing compounds.Type: GrantFiled: May 15, 1978Date of Patent: June 24, 1980Assignee: Lever Brothers CompanyInventors: Eddie N. Gutierrez, Vincent Lamberti
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Patent number: 4194053Abstract: A diester of .alpha.-acetyl-.alpha.'-methyl succinic acid is prepared in improved yield under substantially anhydrous process conditions which minimizes decomposition of that diester by reacting an acetoacetate ester with an .alpha.-halopropionate ester in a solvent containing a nonpolar, aprotic liquid at from about 50.degree. C. to reflux temperature in the presence of a phase transfer agent, a catalytic amount of iodide ion and solid form, substantially anhydrous alkali metal base or basic salt having a high surface area (a size of about 60 mesh or smaller). The resulting diesters can also be used under the stabilizing reaction mixture conditions of this invention as intermediates in processes for making ibuprofen by combining and reacting the .alpha.-acetyl-.alpha.'-methylsuccinate diester with vinyl isobutyl ketone, (or the corresponding Mannich base plus an alkylating agent) and an alkali metal base for a time sufficient to form a reaction mixture containing the .alpha.-methyl-.alpha.'-acetyl-.alpha.Type: GrantFiled: September 1, 1978Date of Patent: March 18, 1980Assignee: The Upjohn CompanyInventor: David R. White
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Patent number: 4189596Abstract: 2-Aryl-C.sub.2 to C.sub.5 -alkanoic acids and esters thereof are prepared by heating a 2-(2-oxo-3-cyclohexenyl)-alkanoic acid or ester derivative in the presence of a sulfonic acid or a phosphonic acid at 75.degree. C. to 130.degree. C. while providing a means for removing water from the reaction mixture. In the process new butenolide derivative intermediates have been discovered. Alternatively, the 2-aryl-C.sub.2 to C.sub.6 -alkanoic acids can be prepared from the butenolides by forming a mixture of the 2-(2-oxo-3-cyclohexenyl)-alkanoic acid with acetic anhydride in the presence of an acid scavenging base, allowing the mixture to stand for a time sufficient to form an acetate intermediate, heating the resulting mixture to about 75.degree. C. to about 130.degree. C. to form the betenolide intermediates. Thereafter these intermediates can be heated with sulfonic or phosphonic acid as above while removing water to form the 2-aryl-C.sub.2 to C.sub.Type: GrantFiled: May 2, 1977Date of Patent: February 19, 1980Assignee: The Upjohn CompanyInventor: Verlan H. VanRheenen
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Patent number: 4173707Abstract: A cyclopentanol derivative represented by the formula ##STR1## wherein R.sub.1 and R.sub.2 are lower straight-chain or branched-chain alkyl, alkenyl or aralkyl, and R.sub.4 is 2-pentenyl or 2-pentynyl, and process for preparing the same.Type: GrantFiled: June 8, 1978Date of Patent: November 6, 1979Assignee: Otsuka Kagaku Yakuhin Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Yuichi Kobayashi
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Patent number: 4172208Abstract: The compound of the formula: ##STR1## is useful as an intermediate to prepare a compound having the generic formula ##STR2## wherein X is selected from groups to provide tetrahydropyran type compounds, 1,4 dioxane type compounds or tetrahydrofuran type compounds, and R is selected from the group consisting of alkali metal, NH.sub.4.sup.+, NH(CH.sub.2 CH.sub.2 OH).sub.3.sup.+, and lower alkyl, branched or straight chain, with up to about C.sub.20 in the chain, useful as a detergent builder.Type: GrantFiled: July 27, 1978Date of Patent: October 23, 1979Assignee: Monsanto CompanyInventors: Marvin M. Crutchfield, Kent P. Lannert
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Patent number: 4146543Abstract: Novel polyfunctional compounds and a process for their preparation are disclosed. These compounds and their alkali metal salts are useful metal sequestrants and/or detergent builders. Selected compounds are also intermediates useful in the syntheses of aconitic acid as well as isocitric and alloisocitric acids and their lactones. The novel polyfunctional compounds are obtained from the reaction of maleic anhydride with selected active methylene or methine containing compounds.Type: GrantFiled: November 4, 1977Date of Patent: March 27, 1979Assignee: Lever Brothers CompanyInventor: Eddie N. Gutierrez
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Patent number: 4123458Abstract: Novel polyfunctional compounds and a novel process for their preparation are disclosed. These compounds may be converted into the acid or salt forms of cis and trans aconitic acids as well as into a racemic mixture of isocitric acid, alloisocitric acid and the lactones of isocitric acid and alloisocitric acid and their salts. All of the acid and salt forms produced are useful as metal sequestrants and/or detergent builders. The novel polyfunctional compounds can also be saponified to their corresponding alkali metal salts which, in turn, are also metal ion seqestering agents and detergent builders. The polyfunctional compounds are the reaction products obtained from the reaction of selected salts of monoalkyl esters of maleic acid with selected active hydrogen containing compounds.Type: GrantFiled: December 22, 1975Date of Patent: October 31, 1978Assignee: Lever Brothers CompanyInventors: Eddie N. Gutierrez, Vincent Lamberti
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Patent number: 4120874Abstract: A compound of the formula ##STR1## wherein R' is lower alkyl, is useful as an intermediate in the preparation of a corresponding tricarboxylate, which is a useful detergent builder.Type: GrantFiled: January 5, 1977Date of Patent: October 17, 1978Assignee: Monsanto CompanyInventors: Marvin M. Crutchfield, Kent P. Lannert