Saturated Lower Fatty Acids Patents (Class 562/606)
  • Patent number: 6258980
    Abstract: There is described a process for the production of a substantially anhydrous salt of an organic acid which comprises reacting a basic compound of a metal with the appropriate organic acid, removing a substantial proportion of water present so as to produce the salt or its hydrate as a liquid phase and then dissolving the liquid phase in a non-aqueous solvent.
    Type: Grant
    Filed: June 27, 1994
    Date of Patent: July 10, 2001
    Assignee: Contracts Chemicals Ltd.
    Inventor: David Anthony Jones
  • Patent number: 6201021
    Abstract: Formula (I) compounds: wherein R1 is alkyl substituted by fluorine(s); R2 is hydroxy, alkoxy, alkoxy substituted by phenyl, NR3R4, in which R3, R4 is (i) hydrogen, (ii) alkyl, (iii) phenyl, (iv) phenyl substituted by alkoxy or carboxyl, (v) heterocyclic ring containing nitrogen atom, (vi) alkyl substituted by phenyl, phenyl subsituted by alkoxy or carboxyl, heterocyclic ring containing nitrogen atom, (vii) the nitrogen bonded to R3 and R4, taken together is a saturated heterocyclic ring or amino acid residue; and non-toxic salts and acid addition salts thereof.
    Type: Grant
    Filed: July 23, 1996
    Date of Patent: March 13, 2001
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Shuichi Ohuchida, Kazuo Kishimoto, Narito Tateishi, Hiroyuki Ohno
  • Patent number: 6077542
    Abstract: Substances that are solid at 25.degree. C. are obtained by dissolving sodium valproate in heated valproic acid and cooling the resultant solution. The resulting solid substances can easily be processed into solid pharmaceutical dosage forms.
    Type: Grant
    Filed: July 31, 1997
    Date of Patent: June 20, 2000
    Inventor: Bernard Charles Sherman
  • Patent number: 6043392
    Abstract: This invention provides a method for thermally converting volatile fatty acid (VFA) salts to ketones by mixing dry calcium salts of VFAs with hot heat transfer agent in an evacuated container, thereby causing thermal decomposition of the calcium salts of VFAs to form ketone-containing vapor and calcium carbonate; and separating the ketone-containing vapor from the calcium carbonate and heat transfer agent by condensing a mixture of ketones from the ketone-containing vapor. This invention also provides a process for conversion of VFA salts, produced by anaerobic fermentation of cellulosic biomass, into liquid fuels, volatile fatty acids, aldehydes, alcohols, and lactic acid.
    Type: Grant
    Filed: June 30, 1997
    Date of Patent: March 28, 2000
    Assignee: Texas A&M University System
    Inventors: Mark T. Holtzapple, Richard R. Davison
  • Patent number: 6013816
    Abstract: Process for the preparation of a linear .omega.-formyl-carboxylic acid or a corresponding linear formylnitrile compound starting from an internally unsaturated C.sub.4 -C.sub.12 carboxylic acid or a corresponding ester or nitrile by means of hydroformylation in the presence of carbon monoxide, hydrogen and a catalyst system, wherein the hydroformylation is carried out in an aqueous medium and in that the catalyst system comprises platinum and a water-soluble organic bidentate ligand.
    Type: Grant
    Filed: July 5, 1996
    Date of Patent: January 11, 2000
    Assignee: DSM NV
    Inventors: Onko J. Gelling, Imre Toth
  • Patent number: 5990351
    Abstract: A process for recovering 2,2-dimethylpropanoic acid in highly pure form from a mixture of 2,2-dimethylpropanoic acid and impurities which may be obtained in the production of a beta lactam antibiotic, by degrading impurities and separating off the volatile fragments.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: November 23, 1999
    Assignee: Biochemie GmbH
    Inventors: Joan Cabre, Victor Centellas, Jose Diago, Asuncion Esteve, Joan Serrat
  • Patent number: 5969183
    Abstract: Provided is a process for producing acetic acid by carrying out reaction of methyl formate in the presence of a Group VIII metal catalyst, at least one iodine compound, acetic acid and carbon monoxide, continuously drawing a reaction mixture from a reactor, introducing the reaction mixture into a flash distillation zone, separating an evaporated component and an unevaporated component, recycling the unevaporated component to the reaction zone, and obtaining acetic acid from the evaporated component, wherein formic acid and methyl formate are allowed to coexist in the flash distillation zone and/or the recycling zone. According to this process, no loss of methyl formate and formic acid is caused and only methyl formate is used as a starting material with basically requiring no supply of carbon monoxide.
    Type: Grant
    Filed: March 2, 1998
    Date of Patent: October 19, 1999
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Futoshi Kawataka, Yoshikazu Shima, Kenichi Nakamura
  • Patent number: 5962735
    Abstract: A solution is provided to the long sought inorganic alternative to resin based adsorbents for iodide clean-up service for corrosive organic liquid. The solution involves the use of a solid inorganic adsorbent comprising a combination of a silica-rich zeolite molecular sieve, which has been cation-exchanged with an iodide-reactive metal selected from silver, mercury, copper, lead, thallium, palladium or mixtures thereof, with a substantially insoluble, porous refractory inorganic oxide binder. Reactivation and regeneration technique for the spent inorganic adsorbent are also covered.
    Type: Grant
    Filed: March 6, 1998
    Date of Patent: October 5, 1999
    Assignee: UOP LLC
    Inventors: Santi Kulprathipanja, Benjamin C. Spehlmann, Richard R. Willis, John D. Sherman, William A. Leet
  • Patent number: 5942237
    Abstract: A novel type of formulation for the topical administration of antigens and/or vaccines to mammals via mucosal membranes comprising one or more adjuvants/vehicles selected from (a) polyoxyethylene sorbitan monoesters, (b) polyoxyethylene castor oil, (c) caprylic/capric acid glycerides and (d) gangliosides in an amount of 0.01 to 15% (v/v) calculated on the total volume of the preparation. This formulation enhances the immunological response n a mammal following mucosal administration, e.g. nasal, oral, rectal or vaginal application.
    Type: Grant
    Filed: October 6, 1995
    Date of Patent: August 24, 1999
    Assignee: Lyfjathroun H.F.
    Inventors: Sveinbjorn Gizurarson, Iver Heron
  • Patent number: 5907060
    Abstract: The present invention relates to a novel process for preparing 3,3-dimethylbutyric acid by reaction of trimethylpyruvic acid with hydrazine hydrate and treatment of the resulting hydrazone with a base.
    Type: Grant
    Filed: June 4, 1998
    Date of Patent: May 25, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventor: Uwe Stelzer
  • Patent number: 5891921
    Abstract: Wood preservative systems comprising (a) a biocidal effective amount of (i) at least one di C.sub.8 -C.sub.12 alkyl quaternary ammonium carboxylate having the formula ##STR1## wherein R.sup.1 and R.sup.2 are a C.sub.8 -C.sub.12 alkyl group; R.sup.3 is a substituted or unsubstituted, interrupted or uninterrupted C.sub.1 -C.sub.100 group; l and q independently are 1, 2 or 3 and (l) (q) is 1, 2, or 3; and n is 0 or an integer from 1 to 50; (ii) at least one di C.sub.8 -C.sub.12 alkyl quaternary ammonium borate having the formula ##STR2## wherein R.sup.1 and R.sup.2 are defined as above, and a is 2 or 3, but when a is 2, b is 0 or 1, and when a is 3, b is 0, 1, or 2; or (iii) a combination of (i) and (ii); and (b) a solvent are provided. These carboxylate quats as well as carboxylate quats wherein R.sup.1 is a C.sub.1 -C.sub.20 alkyl or aryl-substituted alkyl group and R.sup.2 is a C.sub.8 -C.sub.20 alkyl group are preferably prepared by an indirect or a direct synthesis.
    Type: Grant
    Filed: April 18, 1996
    Date of Patent: April 6, 1999
    Assignee: Lonza Inc.
    Inventor: Leigh E. Walker
  • Patent number: 5877349
    Abstract: This process for the synthesis of 3-mercaptopropionic acid by an addition reaction of H.sub.2 S with acrylic acid is carried out in the presence of a solid support having basic guanidine functional groups, provided that the latter do not contain hydrogen bonded directly to a nitrogen atom.
    Type: Grant
    Filed: September 19, 1997
    Date of Patent: March 2, 1999
    Assignee: Elf Acquitaine Exploration Production France
    Inventor: Emmanuel Arretz
  • Patent number: 5856569
    Abstract: A process for making valproic acid from an alkyl alkanoylacetate is disclosed. The alkyl alkanoylacetate is reacted with an n-propyl halide in a biphasic system in the presence of a base and a phase transfer catalyst. The product mixture is acidified to convert the resulting valproate salt into valproic acid.
    Type: Grant
    Filed: October 1, 1997
    Date of Patent: January 5, 1999
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Mose Santaniello, Carlo Alberto Bagolini, Agostino Uttaro, Silverio Fontana
  • Patent number: 5821382
    Abstract: In order to manufacture a thiol compound by causing reaction between an unsaturated compound and hydrogen sulfide, the unsaturated compound and the thiol compound being expressed by following formulas (1) and (2), respectively:CH.sub.2 .dbd.CR.sup.1 --COOR.sup.2 (1)HS--CH.sub.2 --CHR.sup.1 --COOR.sup.2 (2)where R.sup.1 represents a hydrogen atom or a methyl group, and R.sup.
    Type: Grant
    Filed: October 16, 1997
    Date of Patent: October 13, 1998
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Youichi Hino, Ryuichi Ishikawa, Norihiro Wakao
  • Patent number: 5801274
    Abstract: N-?Mercaptoacyl(amino acid or peptide)! compounds and S-lipophilic aliphatic carbonyl derivatives thereof, and pharmaceutical compositions comprising such compounds, as well as the use of these compounds as antihypertensives by the inhibition of neutral endopeptidase and/or peptidyldipeptidase A are disclosed. Methods for preparing such compounds and derivatives are disclosed also.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: September 1, 1998
    Assignee: Institut National de la Sante et de la Recherche Medicale
    Inventors: Marie-Claude Fournie-Zaluski, Bernard-Pierre Roques
  • Patent number: 5786380
    Abstract: The invention provides compounds which are effective antiepileptics and at the same time display only a slight sedative and teratogenic effect and have the formula ##STR1## where the compounds of the formulae (I) and (II) can also be mono- or polyunsaturated, in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each, independently of one another, hydrogen or a C.sub.1 -C.sub.6 -alkyl group, R.sup.5 is hydrogen or a C.sub.1 -C.sub.2 -alkyl group, and at least one of the radicals R.sup.1 to R.sup.4 in the compounds of the formulae (I) and (II) is different from hydrogen, where the compounds of the formula (I), in the case where a center of asymmetry is present on the carbon atom in position 2, and the compounds of the formulae (II), (III) and (IV) are in the form of their racemate, their pure enantiomers or a mixture of their enantiomers which differs from the racemate, and pharmaceutically compatible salts thereof.
    Type: Grant
    Filed: November 23, 1994
    Date of Patent: July 28, 1998
    Inventors: Heinz Nau, Ursula Bojic, Ralf-Siegbert Hauck, Mohamed Mohey Eldin Elmazar
  • Patent number: 5756752
    Abstract: Substituted oxadiazolones of the formula (I) ##STR1## in which R represents optionally substituted alkyl, are obtained in good yields and high purity on reacting in a first step carboxylic acids of the general formula (II)R--COOH (II)with hydrazine hydrate in the presence of a catalyst and an inert diluent at temperatures between 0.degree. C. and 150.degree. C. with elimination of water and removal of said catalyst and reacting the resulting carboxylic hydrazides of the general formula (III)R--CO--NH--NH.sub.2 (III)in a second step with phosgene (COCl.sub.2) at temperatures between 20.degree. C. and 120.degree. C.
    Type: Grant
    Filed: April 15, 1997
    Date of Patent: May 26, 1998
    Assignees: Bayer Corporation, Bayer Aktiengesellschaft
    Inventors: Hans Joachim Diehr, Reinhard Lantzsch, Jacqueline M. Applegate, Klaus Jelich
  • Patent number: 5750571
    Abstract: 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: Grant
    Filed: December 23, 1996
    Date of Patent: May 12, 1998
    Assignee: Genzyme Corporation
    Inventors: Seng Hing Cheng, Shaona Lee Fang, Henry Hoppe, IV, Alan Edward Smith
  • Patent number: 5719290
    Abstract: Novel derivatives of fatty acid analogs that have from one to three heteroatoms in the fatty acid moiety which can be oxygen, sulfur or nitrogen, are disclosed in which the carboxy-terminus has been modified to form various amides, esters, ketones, alcohols, alcohol esters and nitriles thereof. These compounds are useful as substrates for N-myristoyltransferase (NMT) and/or its acyl coenzyme, and as anti-viral and anti-fungal agents or pro-drugs of such agents. Illustrative of the disclosed compounds are fatty acid amino acid analogs of the structure ##STR1## in which X is the ethyl or t-butyl ester of an amino acid such as Gly, L-Ala, L-Ile, L-Phe, L-Try, L-Thr, or an amide such as NHCH.sub.2 C.sub.6 H.sub.5 or NH(CH.sub.2).sub.2 C.sub.6 H.sub.5.
    Type: Grant
    Filed: November 4, 1996
    Date of Patent: February 17, 1998
    Assignee: G. D. Searle & Co.
    Inventors: Sean T. Nugent, Richard A. Mueller
  • Patent number: 5679697
    Abstract: Novel palladium complexes and pharmaceutical compositions comprising the same are provided. Such complexes comprise (palladium).sub.m (lipoic acid).sub.n, wherein m and n are each independently 1 or 2. A process for preparing such complexes is also disclosed. In addition, a method of treatment of tumors and a method of treatment of psoriasis comprising administering the pharmaceutical compositions of the present invention are provided.
    Type: Grant
    Filed: October 18, 1995
    Date of Patent: October 21, 1997
    Inventor: Merrill Garnett
  • Patent number: 5674898
    Abstract: 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: Grant
    Filed: June 7, 1993
    Date of Patent: October 7, 1997
    Assignee: Genzyme Corporation
    Inventors: Seng Hing Cheng, Shaona Lee Fang, Henry Hoppe, IV, Alan Edward Smith
  • Patent number: 5672746
    Abstract: Neurotrophic and antiproliferative compounds related to the antiepileptic drug valproate are provided. These compounds are useful for promoting neuronal function as in neurodegenerative disorders and for treating neoplastic disease.
    Type: Grant
    Filed: August 30, 1994
    Date of Patent: September 30, 1997
    Assignees: American Biogenetic Sciences, Inc., University College Dublin
    Inventors: Heinz Nau, Ciaran M. Regan
  • Patent number: 5663430
    Abstract: In a process for purifying a carboxylic acid fraction obtained by liquid phase carbonylation of an alkyl alcohol and/or its reactive derivative in which volatile iridium- and/or volatile co-promoter contaminants are converted to involatile forms by contacting with an iodide in the absence of carbon monoxide or at a partial pressure less than that of the carbonylation reaction. The involatile contaminants are then separated from the carboxylic acid.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: September 2, 1997
    Assignee: BP Chemicals Limited
    Inventors: George Ernest Morris, Stephen James Smith, John Glenn Sunley, Robert John Watt, Bruce Leo Williams
  • Patent number: 5604032
    Abstract: A fluorine-containing carboxylic acid amine salt of Formula A below: ##STR1## wherein R.sup.1 denotes an aliphatic alkyl group or an aliphatic alkenyl group with 6 to 30 carbons; R.sup.2 denotes a group selected from the group consisting of a fluoroalkyl group with 3 to 30 carbons, a fluoroalkenyl group with 3 to 30 carbons, a fluorophenyl group with 6 to 18 carbons, and a fluoroalkylether group with 5 to 50 carbons; R.sup.3 and R.sup.4 each denotes a saturated or unsaturated hydrocarbon chain with 1 to 20 carbons; R.sup.5 denotes either a fluoroalkyl group with 3 to 30 carbons or a fluoroalkenyl group with 3 to 30 carbons; n denotes 0 or 1; X denotes hydrogen or -(R.sup.6) -R.sup.7 ; and Y denotes hydrogen or -(R.sup.8) -R.sup.9, where R.sup.6 and R.sup.8 each denotes a saturated or unsaturated hydrocarbon chain with 1 to 20 carbons, and R.sup.7 and R.sup.9 each denotes a fluoroalkyl group with 3 to 30 carbons or a fluoroalkenyl group with 3 to 30 carbons.
    Type: Grant
    Filed: October 13, 1994
    Date of Patent: February 18, 1997
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Yoshiaki Kai, Yukikazu Ohchi
  • Patent number: 5599979
    Abstract: Formic acid is difficult to separate from acetic acid by conventional distillation or rectification because of the close proximity of their boiling points. Formic acid can be readily separated from acetic acid by using extractive distillation. Effective agents are propionic acid, butyric acid, valeric acid and 2-ethyl hexanoic acid.
    Type: Grant
    Filed: September 8, 1995
    Date of Patent: February 4, 1997
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5563295
    Abstract: A process for the production of an optically active carboxylic acid (I), which comprises subjecting an olefinic carboxylic acid (II) to asymmetric hydrogenation using a complex as a catalyst consisting of an optically active phosphine (III) and a ruthenium compound.Complex of ##STR1## with a ruthenium compound ##STR2## According to the process of the present invention, optically active carboxylic acids can be produced with high yield.
    Type: Grant
    Filed: March 7, 1995
    Date of Patent: October 8, 1996
    Assignee: Takasago International Corporation
    Inventors: Hidemasa Takaya, Xiaoyong Zhang, Kazuhiko Matsumura, Noboru Sayo, Hidenori Kumobayashi
  • Patent number: 5534651
    Abstract: .gamma.-Mercaptocarboxylic acids and their derivatives, in particular esters and amides, are prepared from .gamma.-butyrolactones via the corresponding thiolactones. The thiolactones are obtained by reaction of a .gamma.-lactone with thiocarboxylates in polar solvents and are converted by ring opening using nucleophilic reagents, such as, alkali metal alkoxides, into the .gamma.-mercaptocarboxylic acid derivatives. These are intermediates, for example, for the synthesis of leucotriene antagonists.
    Type: Grant
    Filed: August 30, 1994
    Date of Patent: July 9, 1996
    Assignee: Lonza Ltd.
    Inventors: Wilhelm Quittmann, John McGarrity
  • Patent number: 5502248
    Abstract: A process for the continuous hydrolysis of esters containing from 2 to about 16 carbon atoms to form at least one alcohol and at least one carboxylic acid and the concurrent separation of the hydrolysis products has been developed. The process uses a solid bed which acts as a catalyst for hydrolysis and as an adsorbent for at least one class of the products. The process 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 a hydrolysis catalyst and at least one solid effective as an alcohol or carboxylic acid adsorbent. Another specific embodiment is one where the simulated moving bed is a strongly acidic macroreticular polymeric resin effective both as a hydrolysis catalyst and as an adsorbent for at least one hydrolysis product.
    Type: Grant
    Filed: February 27, 1995
    Date of Patent: March 26, 1996
    Assignee: UOP
    Inventors: Gregory A. Funk, Hemant W. Dandekar, Simon H. Hobbs
  • Patent number: 5463093
    Abstract: Novel palladium complexes and pharmaceutical compositions comprising the same are provided. Such complexes comprise (palladium).sub.m (lipoic acid).sub.n, wherein m and n are each independently 1 or 2. A process for preparing such complexes is also disclosed. In addition, a method of treatment of tumors and a method of treatment of psoriasis comprising administering the pharmaceutical compositions of the present invention are provided.
    Type: Grant
    Filed: November 26, 1993
    Date of Patent: October 31, 1995
    Inventor: Merrill Garnett
  • Patent number: 5430185
    Abstract: A process is provided for making bulk calcium magnesium acetate in a substantially pure crystalline form. The crystalline CMA contains less than about 0.5% of water soluble impurities.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: July 4, 1995
    Assignee: General Atomics International Services Corporation
    Inventor: Fu Su
  • Patent number: 5414116
    Abstract: The invention relates to a catalyst formed of an active charcoal support in the form of particles or of cylinders having a diameter from 0.3 to 1.5 mm and a length of 0.3 to 5 mm or spheres having a diameter from 0.3 to 2 mm, the said particles being loaded with a precious metal from group 8. Advantageously, palladium on active charcoal is used.The invention is particularly useful for purifying monochloroacetic acid.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: May 9, 1995
    Assignee: Societe Elf Atochem S.A.
    Inventor: Yves Correia
  • Patent number: 5414108
    Abstract: The subject matter of the invention is a process for the preparation of carboxylic acids and derivatives of them of the general formula ##STR1## wherein R means hydrogen, or a C.sub.1-4 alkyl or a (C.sub.1-5 alkoxy)carbonyl group,R.sub.1 is as defined in claim 1,R.sub.7 stands for hydrogen or a C.sub.1-7 alkyl group andR.sub.8 means hydrogen or a carboxyl group.
    Type: Grant
    Filed: August 11, 1992
    Date of Patent: May 9, 1995
    Assignee: Biogal Gyogyszergrar
    Inventors: Gyorgy Toth, Janos Balint, Klara Elek nee Herczik, Zsuzsanna Moricz nee Garai, Eva Mudra nee Kantor
  • Patent number: 5393924
    Abstract: Acylamides or amine acylate salts of arylalkanolamines are prepared by reacting an arylisonitrosoalkanone with hydrogen and a carboxylic acid, carboxylic acid anhydride or carboxylic acid ester or mixture thereof in the presence of a transition metal catalyst; optionally the product is converted to the corresponding arylalkanolamine hydrochloride salt by reaction of the acylamide or amine acylate salt of the arylalkanolamine with hydrogen chloride in a C.sub.1 -C.sub.3 alkyl alcohol.
    Type: Grant
    Filed: April 29, 1994
    Date of Patent: February 28, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: Ahmed M. Tafesh, Olan S. Fruchey, Charles B. Hilton
  • Patent number: 5350872
    Abstract: The subject matter of the invention is a process for the preparation of carboxylic acids and derivatives of them of the general formula ##STR1## wherein R means hydrogen, or a C.sub.1-4 alkyl or a (C.sub.1-5 alkoxy)carbonyl group,R.sub.1 is as defined in claim 1,R.sub.7 stands for hydrogen or a C.sub.1-7 alkyl group andR.sub.8 means hydrogen or a carboxyl group,by reacting a 1,3-dioxane-4,6-dione derivative of the general formula ##STR2## wherein R.sub.9 stands for a C.sub.1-4 alkyl group or a phenyl group, optionally monosubstituted by halogen andR.sub.10 stands for hydrogen or a C.sub.1-5 alkyl group orR.sub.9 and R.sub.10 together form a pentamethylene group,and an aldehyde or ketone of the general formula ##STR3## in the presence of formic acid.
    Type: Grant
    Filed: October 29, 1993
    Date of Patent: September 27, 1994
    Assignee: Biogal Gyogyszergrar
    Inventors: Gyorgy Toth, Janos Balint, Klara Elek nee Herczik, Zsuzsanna Moricz nee Garai, Eva Mudra nee Kantor
  • Patent number: 5344975
    Abstract: A process for production of lower alkanoic acids. A reaction mixture comprising a substituted malonic acid, an acid catalyst, and a limited amount of water is heated to a temperature sufficient to hydrolyze and decarboxylate the ester. The reaction mixture is maintained at the temperature by periodic addition of limited amounts of water, and the reaction is continued for a period of time sufficient to remove substantially all of the alcohol and carbon dioxide generated by the hydrolysis reaction, thereby converting substantially all of the ester to alkanoic acid. The process is particularly useful for the production of valproic acid.
    Type: Grant
    Filed: September 3, 1993
    Date of Patent: September 6, 1994
    Assignee: Wyckoff Chemical Company, Inc.
    Inventor: Andrew G. Zeiler
  • Patent number: 5334758
    Abstract: A process for preparing an optically active carboxylic acid is disclosed, comprising asymmetric hydrogenation of an .alpha.,.beta.-unsaturated carboxylic acid using an alcohol as a hydrogen donor in the presence of a metal-optically active phosphine complex. A carboxylic acid having high optical purity can easily be obtained in a high yield without using specific equipment as required in using hydrogen gas as a hydrogen donor.
    Type: Grant
    Filed: September 30, 1993
    Date of Patent: August 2, 1994
    Assignee: Takasago International Corporation
    Inventors: Masahiko Saburi, Masamichi Ohnuki, Yasuzo Uchida
  • Patent number: 5331011
    Abstract: Disclosed is an N-benzyl-N-phenoxyethylamine selected from the group consisting of the N-benzyl-N-phenoxyethylamine represented by the following formula (I): ##STR1## and an agriculturally acceptable acid addition salt represented by the following formula (II): ##STR2## wherein m represents a number of 1 or 2 with a proviso that when m is 1 and a chlorine atom in the ring A is present at para(4)-position of the ring A, two chlorine atoms in the ring B are present at 2,3-, 2,5-, 2,6-, 3,4- or 3,5-positions of the ring B, and HX represents an acid.
    Type: Grant
    Filed: April 7, 1993
    Date of Patent: July 19, 1994
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Mitsunori Oda, Kazutoshi Kikkawa, Akinori Tanaka, Satoko Imaruoka, Shigeo Yoshinaka
  • Patent number: 5329045
    Abstract: A process for deodorizing a mercapto acid or a polar solvent solution thereof includes extracting malodorous compounds present therein by extraction with carbon dioxide in gaseous, liquid or solid form. The mercapto acid has the formula HS-A-COOH wherein A represents ##STR1## wherein n is an integer ranging from 1-4 and R is linear or branched C.sub.1 -C.sub.3 alkyl.
    Type: Grant
    Filed: April 12, 1993
    Date of Patent: July 12, 1994
    Assignee: L'Oreal
    Inventors: Michel Dedieu, Herve Burgaud, Eric LaPoirie, Veronique Gurfein, Gerard Malle
  • Patent number: 5292928
    Abstract: In a process for reacting a low molecular weight hydroxy compound with a carboxylic acid halide, a small amount of the acid halide is introduced into the reaction vessel and the remainder of the acid halide and the hydroxy compound are added gradually in an approximately stoichiometric ratio. The hydrogen halide formed is thus prevented from dissolving in the reaction medium. The heat of reaction to be dissipated is negligible.
    Type: Grant
    Filed: July 31, 1992
    Date of Patent: March 8, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Karlheinz Miltenberger
  • Patent number: 5235102
    Abstract: There is provided a process for the conversion of a feedstream comprising gaseous and/or liquid feed materials to a desired products by means of catalytic distillation employing a catalyst-packing material comprising a rigid, cellular monolith or a rigid, cellular monolith coated with a catalytically-active material.Preferred rigid, cellular monoliths are ceramic honeycomb monoliths.
    Type: Grant
    Filed: November 20, 1990
    Date of Patent: August 10, 1993
    Assignee: Amoco Corporation
    Inventors: David A. Palmer, Gary P. Hagen
  • Patent number: 5212326
    Abstract: This invention concerns certain diethyl- or dipropylacetic acid salts of sodium valproate which have physiological properties similar to those of valproic acid or sodium valproate but show highly superior stability characteristics.
    Type: Grant
    Filed: January 7, 1991
    Date of Patent: May 18, 1993
    Assignee: Abbott Laboratories
    Inventor: Edwin M. Meade
  • Patent number: 5180850
    Abstract: A new crystalline form of magnesium valproate obtained by reacting valproic acid with magnesium alkoxides in alcoholic solution is described.The new crystalline form is endowed with enhanced bioavailability and may be used in a particularly pure form to prepare pharmaceutical compositions which are useful for treating Central Nervous System pathologies.
    Type: Grant
    Filed: December 13, 1990
    Date of Patent: January 19, 1993
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventor: Claudio Cavazza
  • Patent number: 5175322
    Abstract: A continuous process for preparing a metallic soap by a double decomposition process is disclosed, in which an aqueous solution of an alkali soap and an inorganic metal salt are separately fed directly on the surface of the rotating impeller of a mixer to instantaneously mix them together and the resulting metallic soap aqueous slurry is discharged out from the mixer without delay. Metallic soaps free from contamination with unreacted starting materials or by-products can be continuously obtained using small-sized reactor vessels with a reduced energy.
    Type: Grant
    Filed: November 27, 1989
    Date of Patent: December 29, 1992
    Assignee: Nippon Oil and Fats Co., Ltd.
    Inventors: Fumihiko Yoshizawa, Fumio Kikuchi, Seiichi Kojima, Kenichi Yuasa
  • Patent number: 5175363
    Abstract: Disclosed is a method for reducing olefinic impurities in solutions of carboxylic acids and/or anhydrides. The invention is especially useful for removing substantially all, i.e., greater than 90 percent of trace amounts of olefinic impurities.
    Type: Grant
    Filed: January 28, 1991
    Date of Patent: December 29, 1992
    Assignee: Eastman Kodak Company
    Inventors: Joseph R. Zoeller, Regina M. Moncier
  • Patent number: 5166445
    Abstract: Phosphonium salts of the formula ##STR1## wherein A signifies aryl and Y.sup.- signifies C.sub.1 -C.sub.6 -alkanoate or hydroxytrifluoroborate, as well as their manufacture from 3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-ol with a triarylphosphine and with a C.sub.1 -C.sub.6 -alkanoic acid or a boron trifluoride etherate and, if desired after conversion into the phosphonium salt of a strong acid, further reaction to give lycopene.
    Type: Grant
    Filed: January 11, 1990
    Date of Patent: November 24, 1992
    Assignee: Hoffman-La Roche Inc.
    Inventor: Karl Meyer
  • Patent number: 5162214
    Abstract: A method is provided for removing an anion from an aqueous liquid, such as a fermentation broth. The aqueous broth is contacted with a water-immiscible ion exchange liquid to extract the anion from the broth. The anion exchange liquid is then back extracted with an aqueous phase, to remove the anion, preferably for other uses.
    Type: Grant
    Filed: April 5, 1991
    Date of Patent: November 10, 1992
    Assignee: General Atomics International Services Corporation
    Inventor: Gale L. Hubred
  • Patent number: 5142063
    Abstract: The present invention describes novel chiral rhodium-diphosphine complexes having the formula[Rh(X) (Y) (Lp)]owherein X represents a residue of the formula X--COO.sup.- in which Z signifies a group ##STR1## aryl or substituted aryl, wherein R.sup.1, R.sup.2, R.sup.3 =hydrogen, halogen, lower alkyl, aryl-lower alkyl, perfluoro-C.sub.1-20 -alkyl, aryl, substituted aryl, the group --OR.sup.7, --(CH.sub.2).sub.m --COA or AOC--(CF.sub.2).sub.n, with the proviso that at least one of R.sup.1, R.sup.2, and R.sup.3 represents --OR.sup.7, aryl or substituted aryl,R.sup.4, R.sup.5, R.sup.6 =hydrogen, halogen, lower alkyl, aryl-lower alkyl, perfluoro--C.sub.1-20 -alkyl, aryl, substituted aryl, --(CH.sub.2).sub.m --COA or AOC--(CF.sub.2).sub.n,R.sup.7 =hydrogen, lower alkyl, partially or completely halogenated lower alkyl, aryl, substituted aryl or aryl-lower alkyl,A=The residue --OR or NR'.sub.
    Type: Grant
    Filed: November 20, 1990
    Date of Patent: August 25, 1992
    Assignee: Hoffmann-La Roche, Inc.
    Inventors: Emil A. Broger, Yvo Crameri
  • Patent number: 5101070
    Abstract: 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: Grant
    Filed: July 5, 1988
    Date of Patent: March 31, 1992
    Assignee: Nippon Gohsei Kagaku Kogyo Kabushiki Kaisha
    Inventors: Toshio Yamamoto, Akira Yamashita, Noriyoshi Numoto
  • Patent number: 5087728
    Abstract: 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: Grant
    Filed: July 11, 1990
    Date of Patent: February 11, 1992
    Assignee: Takasago International Corporation
    Inventors: Hiroyuki Nohira, Hidemasa Takaya, Akira Miyashita
  • Patent number: 5047583
    Abstract: A carboxylic acid of formula RCO.sub.2 H, for example acetic acid, is prepared from a formate ester of formula HCO.sub.2 R, for example methyl formate, by heating the ester at elevated temperature with an iridium catalyst, a halide promoter and a strong acid. The strong acid is one having a pKa of not greater than 0 in aqueous media for example a sulphonic acid. Addition of the strong acid to the reaction mixture causes an increase in the rate of conversion of formate ester to carboxylic acid.
    Type: Grant
    Filed: July 13, 1984
    Date of Patent: September 10, 1991
    Assignee: BP Chemicals Limited
    Inventor: Peter S. Williams