Patents by Inventor Ralf Pfirmann
Ralf Pfirmann has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Publication number: 20040029723Abstract: The present invention relates to compounds of the formula 1Type: ApplicationFiled: August 1, 2003Publication date: February 12, 2004Applicant: Clariant GmbHInventors: Berthold Schiemenz, Thomas Wessel, Ralf Pfirmann
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Patent number: 6645904Abstract: The present invention relates to compounds of the formula in which one, two or three of the radicals R1, R2, R3 and R4 are where m and n are an integer from 1 to 10, R5, R6, R7 and R8 are, independently of one another, identical or different and are a straight-chain or branched alkyl radical having 1 to 10 carbon atoms, and the remaining radical(s) R1 to R4 are or —NR9R10, where R9 and R10 are identical or different and are a straight-chain or branched alkyl radical having 1 to 10 carbon atoms, and X− is an inorganic or organic anion or an equivalent of a multiply charged inorganic or organic anion. The invention further relates to mixtures of substances comprising compounds of the formula (1), to a process for preparing the compounds of the formula (1) and to the use thereof.Type: GrantFiled: April 30, 2002Date of Patent: November 11, 2003Assignee: Clariant GmbHInventors: Berthold Schiemenz, Thomas Wessel, Ralf Pfirmann
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Publication number: 20020193592Abstract: The present invention relates to compounds of the formula 1Type: ApplicationFiled: April 30, 2002Publication date: December 19, 2002Applicant: Clariant GmbHInventors: Berthold Schiemenz, Thomas Wessel, Ralf Pfirmann
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Patent number: 6465643Abstract: The present invention relates to compounds of the formula in which one, two or three of the radicals R1, R2, R3 and R4 are where m and n are an integer from 1 to 10, R5, R6, R7 and R8 are, independently of one another, identical or different and are a straight-chain or branched alkyl radical having 1 to 10 carbon atoms, and the remaining radical(s) R1 to R4 are or —NR9R10, where R9 and R10 are identical or different and are a straight-chain or branched alkyl radical having 1 to 10 carbon atoms, and X− is an inorganic or organic anion or an equivalent of a multiply charged inorganic or organic anion. The invention further relates to mixtures of substances comprising compounds of the formula (1), to a process for preparing the compounds of the formula (1) and to the use thereof.Type: GrantFiled: July 17, 2000Date of Patent: October 15, 2002Assignee: Clariant GmbHInventors: Berthold Schiemenz, Thomas Wessel, Ralf Pfirmann
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Patent number: 6407029Abstract: The present invention relates to mixtures comprising from 70 to 99.5% by weight of a compound of the formula (R)4P+X− (1) and from 30 to 0.5% by weight of a compound of the formula (R)3P═O (2), where R is in each case a radical and X− is an inorganic or organic anion or the equivalent of a multiply charged inorganic or organic anion, also to a process for preparing the mixtures by reacting a phosphorus pentahalide with pyrrolidine or piperidine in the molar ratio 1:6 to 1:50 in the presence of an inert solvent initially at −20 to 80° C., subsequently continuing the reaction at 90 to 180° C., treating the resulting reaction product at 0 to 80° C. with aqueous alkali at a pH of 7 to 15, and separating aqueous and organic phase from one another, and to the use of the mixtures as catalyst and cocatalyst for phase-transfer reactions, nucleophilic substitution reactions or halogen-fluorine exchange reactions.Type: GrantFiled: July 17, 2000Date of Patent: June 18, 2002Assignee: Clariant GmbHInventors: Berthold Schiemenz, Thomas Wessel, Ralf Pfirmann, Andreas Beck, Walter Hahn
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Patent number: 6362365Abstract: The present invention relates to a process for preparing trifluorobenzoic acids of the formula in which R is a straight-chain or branched alkyl radical having 1 to 6 C-atoms, an unsubstituted phenyl radical, a substituted phenyl radical which contains one or two alkyl or alkoxy groups having in each case 1 to 4 C atoms, or an araliphatic radical having 7 to 12 C atoms, which comprises reacting a compound of the formula in which R1 and R2 are identical or different and are —CN, —COOR3, where R3 is H, Li, Na, K, MgCl, MgBr, MgI, ½Mg, ½Ca or an alkyl radical having 1 to 6 C atoms, or —CONR4R5, where R4 and R5 are identical or different and are an alkyl radical having 1 to 6 C atoms, with at least one organometallic compound of the formula CuR, CuLiR2, MgXR, ZnR3, LiR, AlX2R, AlXR2AlR3 Al2Cl3R3, where R is as defined in formula (1) and X is Cl, Br or I, in the presence of an inert solvent at from −80 to +150° C.Type: GrantFiled: November 3, 1999Date of Patent: March 26, 2002Assignee: Clariant GmbHInventors: Andreas Maier, Ralf Pfirmann
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Patent number: 6348603Abstract: The present invention relates to a process for the preparation of an isochroman-3-one of the formula (I) by reaction of a 1,2-bishalomethylbenzene of the formula (II) in which X is chlorine, bromine or iodine, with carbon monoxide and a compound of the formula (III) R5R6R7C—OH (III) at a CO pressure of 0.1 to 50 MPa and a temperature of 20 to 200° C.Type: GrantFiled: September 25, 2000Date of Patent: February 19, 2002Assignee: Clariant GmbHInventors: Holger Geissler, Ralf Pfirmann
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Patent number: 6187952Abstract: The present invention relates to a process for the preparation of 3-chloro-4-fluorobenzoyl chloride which comprises reacting 4-fluorobenzaldehyde with a chlorinating agent in the presence of a free-radical initiator in the presence or absence of a solvent at from −20 to 200° C. to give 4-fluorobenzoyl chloride, and reacting the 4-fluorobenzoyl chloride with a chlorinating agent in the presence of a chlorination catalyst in the presence or absence of a solvent at from −20 to 200° C. to give 3-chloro-4-fluorobenzoyl chloride.Type: GrantFiled: December 10, 1998Date of Patent: February 13, 2001Assignee: Clariant GmbHInventors: Ralf Pfirmann, Thomas Wessel
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Patent number: 6103659Abstract: Catalyst for halogen-fluorine exchange reactions on aromatics, consisting essentially of a mixture of one or more compounds of the component a) plus at least one compound of the components b), c) and/or d), whereina) is an amidophosphonium salt of the formula (I) ##STR1## where A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5, A.sup.6, A.sup.7, A.sup.8 are, independently of one another, identical or different and are each a straight-chain or branched alkyl or alkenyl having from 1 to 12 carbon atoms, cycloalkyl having from 4 to 8 carbon atoms, an aryl having from 6 to 12 carbon atoms, an aralkyl having from 7 to 12 carbon atoms, or A.sup.1 A.sup.2, A.sup.3 A.sup.4, A.sup.5 A.sup.6, A.sup.7 A.sup.8 are, independently of one another, identical or different and are in each case connected to one another either directly or via O or N--A.sup.9 to form a ring having from 3 to 7 ring atoms, A.sup.9 is an alkyl having from 1 to 4 carbon atoms and B.sup..crclbar.Type: GrantFiled: July 21, 1999Date of Patent: August 15, 2000Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Sergej Pasenok, Wolfgang Appel, Ralf Pfirmann, Thomas Wessel, Thomas Schach, Hans Schubert
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Patent number: 6075152Abstract: The present invention relates to a process for preparing an isochroman-3-one of the formula (I) by reacting a 1,2-bishalomethylbenzene of the formula (II) ##STR1## in which X is chlorine, bromine or iodine with carbon monoxide and water at a CO pressure of from 0.1 to 50 MPa and a temperature of from 20 to 200.degree. C. in the presence or absence of an ionic halide, in the presence of a palladium catalyst and a dipolar aprotic solvent, where in the formulae (I) and (II) the radicals R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another denote:a hydrogen or fluorine atom;a HO.sub.2 CCH.dbd.CH--, NC-- or F.sub.3 C group;an alkyl, alkoxy or acyloxy radical having in each case 1 to 18 carbon atoms; or a C.sub.6 -C.sub.18 -aryloxy, aryl or heteroaryl radical, where the heteroatoms present are 1 to 3 atoms from the group O, N and/or S;a R.sup.5.sub.2 P(.dbd.O)--, R.sup.6 C(.dbd.O)--, R.sup.6 OC(.dbd.O)--, R.sup.6 OC(.dbd.O)CH.dbd.CH--, R.sup.7 C(.dbd.O)--, R.sup.7 OC(.dbd.O)CH.dbd.CH-- or R.sup.7.sub.Type: GrantFiled: April 5, 1999Date of Patent: June 13, 2000Assignee: Clariant GmbHInventors: Holger Geissler, Ralf Pfirmann
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Patent number: 6001831Abstract: A process for producing 1,2,3,4-tetrahydro-2,4-dioxo-quinazoline-1-yl acetic acid derivatives of the formula (I) in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are mutually independently hydrogen, halogen, OH, NO.sub.2, (C.sub.1 -C.sub.6) alkoxy, (C.sub.1 -C.sub.6) alkyl, halogen-substituted (C.sub.1 -C.sub.6) alkyl, R.sup.5 is hydrogen, (C.sub.1 -C.sub.6) alkyl, phenyl where the alkyl or phenyl radical may also be substituted by halogen atoms; in which an anthranilic acid derivative of formula (II), in which R.sup.1 to R.sup.5 have the above meaning and R.sup.6 is hydrogen, (C.sub.1 -C.sub.6) alkyl or phenyl, where the alkyl or phenyl radical may also be substituted by halogen atoms, is reacted with a metal cyanate and hydrogen chloride in the presence of an inert solvent.Type: GrantFiled: May 22, 1998Date of Patent: December 14, 1999Assignee: Clariant GmbHInventors: Theodor Papenfuhs, Ralf Pfirmann, Stefan Krause, Doris Neumann-Grimm
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Patent number: 5973189Abstract: Compounds have the formula (I), ##STR1## in which R stands for straight-chain or branched (C.sub.1 -C.sub.20) alkyl, phenyl or CH.sub.2 phenyl, the alkyl group or phenyl group being optionally substituted by halogen, (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, and R.sup.1, R.sup.2, R.sup.3, R.sup.4 independently represent hydrogen, halogen, OH, NO.sub.2, (C.sub.1 -C.sub.6) alkoxy, (C.sub.1 -C.sub.6) alkyl or halogen-substituted (C.sub.1 -C.sub.6)-alkyl. Also disclosed is a process for preparing these compounds.Type: GrantFiled: July 16, 1998Date of Patent: October 26, 1999Assignee: Clariant GmbHInventors: Theodor Papenfuhs, Ralf Pfirmann, Doris Neumann-Grimm, Stefan Krause
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Patent number: 5965775Abstract: The present invention relates to a process for the preparation of 3,5-difluoroaniline by reacting 3,5-difluorochlorobenzene with ammonia in the presence of a solvent in the presence of a copper compound and at least one metal selected from the group consisting of copper, iron, cobalt, nickel, chromium, molybdenum and zinc, at 100 to 250.degree. C.Type: GrantFiled: May 13, 1998Date of Patent: October 12, 1999Assignee: Clariant GmbHInventors: Ralf Pfirmann, Stefan Krause
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Patent number: 5945556Abstract: A process for preparing N-carboxymethylene-4-chloroanthranilic acid, and its dialkyl esters. The invention relates to a process for preparing N-carboxymethylene-4-chloroanthranilic acid and its dialkyl esters, which comprises reacting 2,4-dichlorobenzoic acid in the presence of a base, of a solvent and of a catalyst with glycine to give N-carboxymethylene-4-chloroanthranilic acid and, where appropriate, reacting the latter in the presence of a base and of a solvent with a dialkyl sulfate, dialkyl carbonate or alkyl halide to give the dialkyl ester.Type: GrantFiled: April 14, 1998Date of Patent: August 31, 1999Assignee: Clariant GmbHInventors: Theodor Papenfuhs, Ralf Pfirmann, Stefan Krause, Doris Neumann-Grimm
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Patent number: 5874608Abstract: The present invention relates to a process for the preparation of compounds of the formula (1)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOR (1)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms or OR, NHR, NR.sub.2, SR or COOR, in which R is an alkyl radical having 1 to 4 carbon atoms, Ar is an aryl radical having 6 to 12 carbon atoms and the radical R shown in formula (1) has the above meaning, by reacting a compound of the formula (2)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOH (2)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms, OH, NH.sub.2, NHR, SH or COOH and Ar has the same meaning as in formula (1), with a sulfate of the formula (RO).sub.2 SO.sub.2, in which R has the above meaning, in the presence of a water-insoluble tertiary amine and water at a temperature of 10.degree.Type: GrantFiled: May 19, 1997Date of Patent: February 23, 1999Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Theodor Papenfuhs
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Patent number: 5849959Abstract: The present invention relates to compounds of the formula (1) ##STR1## where R is H, a straight-chain or branched alkyl radical with 1 to 6 carbons, a fluorinated straight-chain or branched alkyl radical with 1 to 6 carbons, a benzyl radical, or a benzyl radical substituted by an alkyl group or alkoxy group with 1 to 4 carbons each, or by halogen, X is H, Cl, Br or I, and X is different from R, and a process for their preparation.Type: GrantFiled: December 11, 1996Date of Patent: December 15, 1998Assignee: Clariant GmbHInventors: Ralf Pfirmann, Rainer Wingen
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Patent number: 5773651Abstract: Process for the preparation of fluorine-containing compounds by reduction in a container provided with a stirrer, the stirrer being constructed entirely or partly of a carbon material.Type: GrantFiled: November 27, 1996Date of Patent: June 30, 1998Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Friedrich Seitz
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Patent number: 5744628Abstract: The present invention relates to a process for the preparation of compounds of the formula (1)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOR (1)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms, OR, NHR, NR.sub.2, SR or COOR, R being an alkyl radical having 1 to 4 carbon atoms, Ar is an aryl radical having 6 to 12 carbon atoms and the radical R identified in formula (1) has the above meaning, by reacting a compound of the formula (2)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOH (2)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms, OH, NH.sub.2, NHR, SH or COOH and Ar has the same meaning as in formula (1), with a sulfate of the formula (RO).sub.2 SO.sub.Type: GrantFiled: July 29, 1996Date of Patent: April 28, 1998Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Theodor Papenfuhs
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Patent number: 5739388Abstract: The present invention relates to a process for the preparation of compounds of the formula ##STR1## in which the radicals R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are COOH, H, F, Cl, Br, CF.sub.3, OH, an alkoxy or alkyl radical having in each case 1 to 4 carbon atoms or a radical --NR.sup.6 R.sup.7, in which R.sup.6 and R.sup.7 are identical or different and are H, an alkyl radical having 1 to 4 carbon atoms or a phenyl radical, by dissolving in water a compound of the formula ##STR2## in which the radicals R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and have the abovementioned meaning or, in departure therefrom, instead of H can be COOH, admixing the aqueous solution with a water-insoluble amine which is inert under the reaction conditions and carrying out the decarboxylation at a pH of 3 to 9 and a temperature of 70.degree. to 210.degree. C.Type: GrantFiled: May 2, 1996Date of Patent: April 14, 1998Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Hans Schubert
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Patent number: 5723658Abstract: The present invention relates to a process for the preparation of salts of substituted or unsubstituted phthalic acids, by reacting a compound of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and are H, F, Cl, Br, CF.sub.3, OH, an alkoxy or alkyl radical in each case having 1 to 4 carbon atoms, or a radical --NR.sup.7 R.sup.8, in which R.sup.7 and R.sup.8 are identical or different and are H, an alkyl radical having 1 to 4 carbon atoms, or a phenyl radical, R.sup.5 and R.sup.6 are identical or different and are H, a --CO-- alkyl group having 1 to 6 carbon atoms in the alkyl radical, or a benzoyl group, or R.sup.5 and R.sup.6 together form a radical of the formula ##STR2## in which R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are identical or different and are H, F, Cl, Br, CF.sub.3, OH, an alkoxy or alkyl radical in each case having 1 to 4 carbon atoms, or a radical --NR.sup.7 R.sup.8, in which R.sup.7 and R.sup.Type: GrantFiled: May 2, 1996Date of Patent: March 3, 1998Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Theodor Papenfuhs