Processes Patents (Class 546/327)
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Patent number: 4970313Abstract: A process for the preparation of optically active 3-de-methylmevalonic acid derivatives, and intermediates A process for the preparation of optically active 3-de-methylmevalonic acid derivatives of the formula I ##STR1## (3,5-dihydroxy carboxylic acid derivatives) or of the formula II ##STR2## (.beta.-hydroxy lactones) in which R, R.sup.1 and Y have the indicated meanings, is described. The invention furthermore relates to aldehydes of the formula XII ##STR3## in which M represents the indicated protective groups. The 3-demethylmevalonic acid derivatives of this invention are useful for lowering cholesterol levels of a host.Type: GrantFiled: December 6, 1988Date of Patent: November 13, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunther Wess, Kurt Kesseler, Ekkehard Baader, Gerhard Beck
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Patent number: 4940808Abstract: A process for the ozonization of unsaturated organic compounds in a reaction column through which the unsaturated compounds--in solution in a protic solvent--and an ozone-containing carrier gas and an inert coolant are passed downward in co-current flow to provide for an improved coolant effect and an increased ozonization yield where the coolant comprises a compound gaseous or liquid at ambient temperature with a boiling point preferably in the range from +20.degree. C. to -200.degree. C. The boiling point of the coolant is preferably at least 5.degree. C. below the ozonization temperature.Type: GrantFiled: July 7, 1988Date of Patent: July 10, 1990Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Paul Schulz, Michael J. Virnig, Franz J. Carduck
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Patent number: 4820823Abstract: In accordance with a process of the present invention, .alpha.-keto acids of the general formula RCOCOOH wherein R is aryl, alkenyl or heterocyclic group, can be obtained through one-step carbonylation reaction of an organic halogenide of the general formula RX wherein R is the same as above and X is a halogen atom, with carbon monoxide and water in the presence of a basic compound and a palladium containing catalyst.Type: GrantFiled: February 21, 1986Date of Patent: April 11, 1989Assignee: Director-General of Agency of Industrial Science and TechnologyInventors: Masato Tanaka, Toshiaki Kobayashi, Toshiyasu Sakakura
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Patent number: 4792606Abstract: A process for the preparation of a dimeric aromatic acyl cyanide of the formula ##STR1## in which Ar is optionally substituted phenyl, naphthyl or hetaryl,comprising reaction an acyl halide of the formulaAr--CO--Halin whichHal is fluorine, chlorine or bromine, with an alkali metal cyanide in a two-phase system comprising water and a water-immiscible or only sparingly water-miscible aliphatic ketone, and in the presence of a phase-transfer catalyst. The products are known intermediates for pesticides.Type: GrantFiled: July 16, 1987Date of Patent: December 20, 1988Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Hermann-Dieter Krall
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Patent number: 4723016Abstract: One-step process for preparing anhydrous, organic acid alkali or alkaline earth metal salts by contacting and reacting an organic or polymeric acid fluoride, anhydride or ester and an organic alkali or alkaline earth metal silanolate.Type: GrantFiled: February 13, 1986Date of Patent: February 2, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventors: Bertrand L. Chenard, Evan D. Laganis
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Patent number: 4691050Abstract: The present invention provides a process for the preparation of aromatic dicarboxylic acids by the carbonylation of aromatic diiodides. The aromatic diiodides are reacted with carbon monoxide in the presence of a soluble rhodium catalyst in a hydrocarbon acid reaction medium to prepare the aromatic dicarboxylic acids.Type: GrantFiled: May 23, 1986Date of Patent: September 1, 1987Assignee: Eastman Kodak CompanyInventors: Carl M. Lentz, James R. Overton, David D. Cornell
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Patent number: 4678509Abstract: Certain novel pyridinyloxyphenoxy alkanoic acids, pyridinylthiophenoxy alkanoic acids, derivatives thereof and related compounds are described. More specifically, these novel compounds bear a fluorine substituent in the 3-position of the pyridinyl group and in the 5-position the substituent is selected from chlorine, CF.sub.3, CF.sub.2 Cl or CF.sub.2 H. These novel compounds exhibit surprising preemergent and postemergent activity in the control of grassy weeds.Type: GrantFiled: November 1, 1985Date of Patent: July 7, 1987Assignee: The Dow Chemical CompanyInventors: Howard Johnston, Lillian H. Troxell
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Patent number: 4663429Abstract: A process for producing a lactone polymer which comprises reacting an ester compound synthesized from an alcohol and an acid or acid anhydride thereof with a lactone and a ring-opening polymerization initiator without being accompanied by condensation. The thus produced lactone polymer is effective for preventing shrinkage of thermosetting resins, particularly unsaturated polyester resins.Type: GrantFiled: July 31, 1985Date of Patent: May 5, 1987Assignee: Daicel Chemical Industries, Ltd.Inventors: Takaaki Murai, Shoji Watanabe, Kimio Inoue, Tomohisa Isobe, Naoki Nakashima, Takuya Miho, Yoshiyuki Ikemoto
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Patent number: 4647691Abstract: Ethyl and n-propyl esters of carboxylic acids are prepared in good yield from methanol, syngas and a carboxylic acid by contacting a mixture of the carboxylic acid, carbon monoxide, hydrogen and methanol with a catalyst composition comprising a ruthenium-containing compound, a cobalt-containing compound and a quaternary onium salt or base, and heating the resulting mixture at an elevated temperature and pressure for sufficient time to produce the desired ethyl and propyl esters, and then recovering the same from the reaction mixture.Type: GrantFiled: January 13, 1982Date of Patent: March 3, 1987Assignee: Texaco Inc.Inventors: Jiang-Jen Lin, John F. Knifton
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Patent number: 4612386Abstract: Carboxylic acid esters are produced by the reaction of a carboxylic acid halide with a carbonate ester in the presence of an initiator. The reaction of a dicarboxylic acid dihalide and a bis(alkyl carbonate) ester produces a polymeric polyester.Type: GrantFiled: December 17, 1981Date of Patent: September 16, 1986Assignee: The Dow Chemical CompanyInventor: James M. Renga
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Patent number: 4565568Abstract: Certain novel pyridinyloxyphenoxy alkanoic acids, pyridinylthiophenoxy alkanoic acids, derivatives thereof and related compounds are described. More specifically, these novel compounds bear a fluorine substituent in the 3-position of the pyridinyl group and in the 5-position the substituent is selected from chlorine, CF.sub.3, CF.sub.2 Cl or CF.sub.2 H. These novel compounds exhibit surprising preemergent and postemergent activity in the control of grassy weeds.Type: GrantFiled: May 23, 1983Date of Patent: January 21, 1986Assignee: The Dow Chemical CompanyInventors: Howard Johnston, Lillian H. Troxell
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Patent number: 4564701Abstract: The present invention provides a process for the preparation of aryl carboxylic acids by the carbonylation of diaryliodonium salts. The diaryliodonium salts are reacted with carbon monoxide in the presence of a zero-valent palladium in a hydrocarbon acid reaction medium to prepare the aromatic carboxylic acids.Type: GrantFiled: January 22, 1985Date of Patent: January 14, 1986Assignee: Eastman Kodak CompanyInventors: Carl M. Lentz, James R. Overton, David D. Cornell
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Patent number: 4549025Abstract: Carboxylic acids having the general formula:R--COOHwherein R is selected from the group consisting of aryl, aralkyl, aralkenyl, aralkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, alkyl, alkenyl and alkynyl, optionally substituted by inert or non-reactive substituents under the reaction conditions, are obtained by oxidation of the corresponding aldehydes with an alkali metal or alkaline-earth metal chlorite in the presence of hydrogen peroxide and in an aqueous-organic solvent. The resulting carboxylic acids are utilizable as intermediates for preparing fine chemicals in known ways.Type: GrantFiled: December 12, 1984Date of Patent: October 22, 1985Assignee: Montedison S.p.A.Inventors: Enrico Dalcanale, Giorgio Bottaccio, Stefano Campolmi, Fernando Montanari
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Patent number: 4540810Abstract: This invention concerns the improved preparation of alkanol and glycol esters, such as ethylene glycol diesters, by reaction of carbon monoxide and hydrogen in the presence of a catalyst system comprising ruthenium and a quaternary aryl or alkaryl phosphonium salt and a liquid phase medium containing a carboxylic acid co-reactant.Type: GrantFiled: September 20, 1979Date of Patent: September 10, 1985Assignee: Texaco Development CorporationInventor: John F. Knifton
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Patent number: 4537970Abstract: This invention relates to the preparation of esters or salts of aromatic or etheroaromatic acids having formula Y--Ar--CO--OR (I), where:Ar represents an aromatic group constituted by one or more benzene rings, optionally condensed, or an etheroaromatic nucleus optionally condensed with one or more benzene rings;Y represents from zero to more substituents, equal or different, chosen among a halogen; an alkyl group having up to 6 carbon atoms; an alkoxy group having up to 5 carbon atoms; an ester group --COOR', where R' contains up to 5 carbon atoms; a hydroxyl group; a phenyloxy group, optionally substituted with groups inert under reaction conditions; a trifluoromethyl group; a nitrile group; an amidic group (--CONH.sub.2); an acetamidic group (--NH--CO--CH.sub.3); or an acyl group --CO--R", where R" represents a hydrocarbon group having up to 8 carbon atoms;R represents an alkyl group R.sub.1 having up to 5 carbon atoms or an alkali metal or alkaline earth metal M.Type: GrantFiled: December 12, 1983Date of Patent: August 27, 1985Assignee: Montedison S.p.A.Inventors: Marco Foa, Franco Francalanci, Andrea Gardano, Elena Bencini
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Patent number: 4517369Abstract: Preparation of mixtures rich in 3,4,5,6-tetrachloro-2-trichloromethyl pyridine by chlorinating 3,4,5-trichloro-2-trichloromethyl pyridine, 3,5-dichloro-2-trichloromethyl pyridine or 5-chloro-2-trichloromethyl pyridine, or mixtures thereof, in the presence of ferric chloride catalyst in the temperature range of from about 170.degree. C. to about 220.degree. C.Type: GrantFiled: September 29, 1982Date of Patent: May 14, 1985Assignee: Kalama Chemical, Inc.Inventors: Michael J. Marinak, John L. Simonson
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Patent number: 4496736Abstract: Carboxylic acids and N-t.-alkylamines can be prepared simultaneously by the alkaline pressure hydrolysis of N-t.-alkyl carboxylic acid amides. A 5 to 50% strength by weight aqueous solution of an alkali metal hydroxide is employed for this purpose in an amount of 1.0 to 1.3 mols per mol of the amide. The process is carried out at 200.degree. to 350.degree. C.Type: GrantFiled: June 3, 1982Date of Patent: January 29, 1985Assignee: Bayer AktiengesellschaftInventors: Gerhard Bonse, Gerhard Marzolph, Heinz U. Blank
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Patent number: 4440946Abstract: This invention is a process for producing a carboxylate ester which involves contacting mixtures of alcohol and aldehyde in vapor phase with a reduced silver-cadmium-zinc-zirconium catalyst composition.Type: GrantFiled: July 26, 1982Date of Patent: April 3, 1984Assignee: Celanese CorporationInventors: Richard H. Summerville, deceased, James E. Summerville, Jr., administrator
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Patent number: 4419515Abstract: This invention relates to a two stage process for preparing 2,6-pyridinedicarboxylic acid or dipicolinic acid from 2,6-dimethyl-pyridine through oxidation of the latter in an acid environment with hexavalent chromium salts and formation of a molar addition compound between dicarboxylic acid, being formed by oxidation, and chromic anhydride in the first stage, and subsequent hot hydrolysis of the addition product so obtained, thus isolating 2,6-pyridinedicarboxylic acid therefrom in the second stage. The invention also comprises the above mentioned intermediate complex addition compound and the 2,6-pyridinedicarboxylic acid of high purity, obtained by the process according to said invention.Type: GrantFiled: July 13, 1981Date of Patent: December 6, 1983Assignee: Luigi Stoppani S.p.A.Inventors: Giovanni Ghelli, Enrico Bruschi, Gino Agnese
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Patent number: 4414410Abstract: Alkyl esters, such as ethyl acetate, are prepared by contacting the corresponding next lower carbon number alkyl ester, such as methyl acetate, with carbon monoxide and hydrogen in the presence of an iodine or iodide-free catalyst composition comprising a ruthenium-containing compound, a cobalt containing compound and a quaternary phosphonium salt or base, and heating the mixture to an elevated temperature and pressure for sufficient time to produce the desired higher alkyl ester, and then recovering the same from the reaction mixture.Type: GrantFiled: January 13, 1982Date of Patent: November 8, 1983Assignee: Texaco Inc.Inventors: Jiang-Jen Lin, John F. Knifton
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Patent number: 4395566Abstract: An improved process for exterifying carboxyaromatics is disclosed wherein an anhydride of a carboxyaromatic, such as pyromellitic dianhydride, is reacted with a fluorinated alcohol and an epoxide to give a mixed ester capable of imparting oil and/or water repellency to textiles. The improvement comprises utilizing the epoxide as the reaction medium to reduce reaction times and waste water treatment requirements.Type: GrantFiled: March 8, 1982Date of Patent: July 26, 1983Assignee: American Hoechst CorporationInventors: James H. Covill, Michael G. Kelly, Thomas F. Leahy
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Patent number: 4336384Abstract: In a new method of producing 4-amino-3,5,6-trichloropicolinic acid 3,4,5,6-tetrachloropicolinonitrile is reacted with ammonium hydroxide, preferably at about 130.degree. C. to about 160.degree. C. The free acid is precipitated upon acidification of the reaction mixture and may be recovered therefrom.Type: GrantFiled: April 23, 1981Date of Patent: June 22, 1982Assignee: The Dow Chemical CompanyInventors: Edwin R. Henson, David J. Koranek
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Patent number: 4334074Abstract: 3,6-Dichloropicolinic acid, a highly active plant growth regulator, is recovered from basic, aqueous solutions thereof by acidification with HCl in the presence of a flocculant, separating the precipitated 3,6-dichloroacid, extracting the unprecipitated acid from the mother liquor with a solvent and stripping the extracted acid from the solvent with another portion of the basic, aqueous feed solution.Type: GrantFiled: February 2, 1981Date of Patent: June 8, 1982Assignee: The Dow Chemical CompanyInventor: Russell R. Peterson
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Patent number: 4237301Abstract: This invention relates to a two stage process for preparing 2,6-pyridin-dicarboxylic acid or dipicolinic acid from 2,6-dimethyl-pyridine through oxidation of the latter in an acid environment with hexavalent chromium salts and formation of a molar addition compound between dicarboxylic acid, being formed by oxidation, and chromic anhydride in the first stage, and subsequent hot hydrolysis of the addition product so obtained, thus isolating 2,6-pyridin-dicarboxylic acid therefrom in the second stage. The invention also comprises the above mentioned intermediate complex addition compound and the 2,6-pyridin-dicarboxylic acid of high purity, obtained by the process according to said invention.Type: GrantFiled: November 30, 1978Date of Patent: December 2, 1980Assignee: Luigi Stoppani S.p.A.Inventors: Giovanni Ghelli, Enrico Bruschi, Gino Agnese
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Patent number: 4217457Abstract: A highly selective oxidation process for preparing pyridin-carboxylic acids from pyridine compounds nucleus substituted with alkyl groups, through a carbon-carbon bond, and oxidizable to carboxyl, and from hydrosoluble hexavalent chromium compounds, in the presence of an acid.Particularly described is the oxidation of beta-picoline with sodium bichromate to obtain the sodium salt of nicotinic acid and 99.5% pure free acid, respectively.Type: GrantFiled: July 14, 1978Date of Patent: August 12, 1980Assignee: Luigi Stoppani S.p.A.Inventor: Giovanni Ghelli
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Patent number: 4138488Abstract: Disclosed herein are substituted diphenylmethyl picolinic acids, pharmaceutically acceptable salts, amides and esters thereof. The compounds disclosed are useful as topical anti-acne agents.Type: GrantFiled: January 10, 1977Date of Patent: February 6, 1979Assignee: Schering CorporationInventors: Margaret H. Sherlock, Heide Roebke
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Patent number: 4129566Abstract: New compounds which have the general formula ##STR1## ARE USEFUL AS HYPOTENSIVE AGENTS.Type: GrantFiled: February 15, 1978Date of Patent: December 12, 1978Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, Sehsea I. Natarajan
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Patent number: RE29981Abstract: A process for the preparation of organic carboxylic acids which comprises converting a formic acid ester expressed by the general formulaHCOORwherein R stands for a chain or cyclic aliphatic hydrocarbon radical which may have an aliphatic unsaturation, an aryl radical, an aralkyl radical or a heterocyclic radical,At an elevated temperature under raised pressure of carbon monixide to an organic carboxylic acid expressed by the general formulaRCOOHwherein R is as defined above.Type: GrantFiled: July 22, 1977Date of Patent: May 1, 1979Assignee: Mitsubishi Gas Chemical Company, Inc.Inventor: Nobuo Isogai