Reactant Contains -coo- Group Patents (Class 568/319)
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Patent number: 5929284Abstract: Processes for efficiently producing .alpha.-halo ketones, .alpha.-halohydrins and epoxides on an industrial scale. The prosesses include one for producing an .alpha.-halo ketone of general formula (3) by decarboxylating a product of reaction between a carboxilic acid derivative of general formula (1) and a metal enolate prepared from an .alpha.-haloacetic acid of general formula (2) or an acceptable salt thereof, one for producing an by reducing the .alpha.-halo ketone (3), and one for producing an epoxide (13) by treating the .alpha.-halohydrin (11) with a base to effect ring closure. The above prosesses are particularly suitable for producing optically active .alpha.-halo ketones, .alpha.-halohydrins and epoxides from the corresponding .alpha.-amino acid derivatives.Type: GrantFiled: December 18, 1996Date of Patent: July 27, 1999Assignee: Kaneka CorporationInventors: Akira Nishiyama, Tadashi Sugawa, Hajime Manabe, Kenji Inoue, Noritaka Yoshida
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Patent number: 5925795Abstract: This invention relates to processes for the preparation of aryl-.beta.-diketones and aryl-pyrimidine ketones. In addition, this invention relates to the preparation of aryl-.beta.-triketones and dimethyl aminomethylene .beta.-diketones, which are useful as crop protection intermediates.Type: GrantFiled: September 16, 1996Date of Patent: July 20, 1999Assignee: Zeneca LimitedInventors: Raymond A. Felix, Hsiao-Ling M. Chin, Frank X. Woolard, David L. Lee
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Patent number: 5852200Abstract: Cross-coupling or addition reactions of organic compounds, including acid halides, allylic halides, and .alpha.,.beta.-unsaturated carbonyl containing compounds, with organozinc compounds may be readily and safely carried out in the presence of cuprous iodide. The use of this catalyst in the coupling reaction provides for the preparation of commercially useful products in the pharmaceutical, agrochemical and other industries.Type: GrantFiled: August 22, 1996Date of Patent: December 22, 1998Assignee: Rieke Metals, Inc.Inventor: Reuben D. Rieke
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Patent number: 5817878Abstract: The present invention concerns a process for the acylation of an aromatic ether.Preferably, the invention relates to a process for the acylation of an unsubstituted aromatic ether, in particular anisole.The acylation process of the invention consists of reacting the ether with an acylation agent in the presence of a zeolitic catalyst, and is characterized in that the acylation reaction is carried out in the presence of an effective quantity of a catalyst comprising a beta zeolite with an atomic ratio denoted "global Si/Me.sup.1 " between the number of atoms of the element silicon and the number of atoms of every trivalent element Me.sup.1 contained in the zeolite of no less than 15, preferably in the range 15 to 55, and more preferably in the range 18 to 35.Type: GrantFiled: January 9, 1997Date of Patent: October 6, 1998Assignee: Rhone-Poulenc ChimieInventors: Michel Spagnol, Laurent Gilbert, Eric Benazzi, Christian Marcilly
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Patent number: 5756814Abstract: (1) CF.sub.2 .dbd.CFO(CF.sub.2).sub.n COOR is allowed to react with chlorine or bromine to obtain CF.sub.2 XCFXO(CF.sub.2).sub.n COOR', (2) which is allowed to react with a Grignard reagent MgBrC.sub.6 H.sub.3 (CH.sub.3).sub.2 to convert the terminal group to --COC.sub.6 H.sub.3 (CH.sub.3).sub.2, (3) followed by reaction with diethylaminosulfur trifluoride to convert --COC.sub.6 H.sub.3 (CH.sub.3).sub.2 to --CF.sub.2 C.sub.6 H.sub.3 (CH.sub.3).sub.2, (4) followed further by oxidation of the resulting methyl group and by esterification to convert the methyl group to --CF.sub.2 C.sub.6 H.sub.3 (COOR).sub.2 and (5) followed by dechlorination or debromination to obtain CF.sub.2 .dbd.CFO(CF.sub.2).sub.n CF.sub.2 C.sub.6 H.sub.3 (COOR).sub.2. The resulting bifunctional vinyl ether compound having an aromatic ring is a novel compound and can be used as a copolymer component for fluorine-containing elastomers.Type: GrantFiled: June 23, 1997Date of Patent: May 26, 1998Assignee: Nippon Mektron, LimitedInventors: Leng-Tain Lin, Kenji Iimura, Takehiro Sonoi
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Patent number: 5750795Abstract: The present invention provides a process for producing a ketone represented by a general formula RCOR' (wherein R is a C.sub.1 -C.sub.17 alkyl group, a C.sub.7 -C.sub.12 aralkyl group, a C.sub.7 -C.sub.12 aryl group or a C.sub.5 -C.sub.8 cycloalkyl group; R' is a C.sub.1 -C.sub.17 alkyl group, a C.sub.7 -C.sub.12 aralkyl group, a C.sub.7 -C.sub.12 aryl group or a C.sub.5 -C.sub.8 cycloalkyl group; R and R' may the same), which process comprises reacting a carboxylic acid represented by a general formula RCOOH (wherein R has the same definition as given above) with a carboxylic acid represented by a general formula R'COOH (wherein R' has the same definition as given above) in a gas phase in the presence of a catalyst containing at least either of MgO and CaO.The process allows for production of an intended ketone at a high yield at high productivity.Type: GrantFiled: January 26, 1996Date of Patent: May 12, 1998Assignee: Nippon Shokubai, Ltd.Inventor: Noboru Saito
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Patent number: 5744071Abstract: The present invention provides processes for making alkynyl ketones and precursors thereof, using less expensive reagents and/or hydrocarbon solvents and/or higher temperatures.Type: GrantFiled: November 19, 1996Date of Patent: April 28, 1998Assignee: FMC CorporationInventors: Philip Franklin Sims, Anne Pautard-Cooper
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Patent number: 5679865Abstract: The invention relates to a process for the preparation of polyhydroxybenzophenones by treating benzoic acid or a derivative thereof with a polyhydroxybenzene or a derivative thereof in the presence of a large pore zeolite as a catalyst.Type: GrantFiled: June 21, 1996Date of Patent: October 21, 1997Assignee: Technische Universiteit DelftInventors: Anthonius Johannes Hoefnagel, Herman van Bekkum
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Patent number: 5637773Abstract: Aromatic ethers/phenols are acylated, characteristically into hydroxy- and/or alkoxyaromatic alkylketones, and in particular, are acylated in the para-position relative to an alkoxy substituent borne by the aromatic nucleus, by reacting/condensing same with an acylation agent, for example acetyl chloride or acetic anhydride, in the presence of a catalytically effective amount of a bismuth halide, or a precursor compound that generates, in situ, a bismuth halide.Type: GrantFiled: August 24, 1995Date of Patent: June 10, 1997Assignee: Rhone-Poulenc ChimieInventors: Jean-Roger Desmurs, Jacques Dubac, Mireille Labrouillere, Andre Laporterie
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Patent number: 5621146Abstract: A process for producing 2,4-dihydroxyacetophenone is provided wherein resorcinol and acetic acid are reacted in the presence of a proton acid catalyst while removing formed water.Type: GrantFiled: December 7, 1995Date of Patent: April 15, 1997Assignee: Kuraray Co., Ltd.Inventors: Takashi Fukumoto, Katsuji Ujita, Toshiki Mori, Kozo Nakao, Yoshin Tamai
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Patent number: 5600013Abstract: Cyclic ketones, notably cyclopentanone and 2,2-dimethylcyclopentanone, are simply, economically and efficiently prepared, even on an industrial scale, by decarboxylating/cyclizing a dicarboxylic acid, in liquid phase, in the presence of a catalytically effective amount of a condensed or uncondensed neutral phosphate.Type: GrantFiled: October 4, 1995Date of Patent: February 4, 1997Assignee: Rhone-Poulenc ChimieInventors: Michel Alas, Michel Crochemore
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Patent number: 5583264Abstract: Described are compounds defined according to the structure: ##STR1## wherein Z represents para cyclohexylene or para phenylene and wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different methyl or hydrogen; and wherein R.sub.4 represents hydrogen, methyl or ethyl with the proviso that the sum of the carbon atoms in R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is 2. Also described are para-C.sub.5 alkyl-substituted ethoxycyclohexanes defined according to the structure: ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 represent the same or different methyl or hydrogen; and wherein R.sub.4 represents hydrogen, methyl or ethyl with the proviso that the sum of the carbon atoms in R.sub.1, R.sub.2, R.sub.3 and R.sub.Type: GrantFiled: February 26, 1996Date of Patent: December 10, 1996Assignee: International Flavors & Fragrances Inc.Inventors: Michael G. Monteleone, Richard A. Weiss, Marc D. Evans, Marie R. Hanna
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Patent number: 5545763Abstract: Described are 1-oxo-substituted and unsubstituted isobutyl-4-ethoxy-benzenes and mixtures thereof with bicyclopentadiene derivatives, wherein the 1-oxo-substituted and unsubstituted isobutyl-4-ethoxy-benzenes are defined according to the structure: ##STR1## wherein Y.sub.1 represents one of the moieties: ##STR2## and wherein the bicyclopentadiene derivatives are defined according to the structure: ##STR3## wherein Z.sub.1 and Z.sub.2 represent hydrogen, C.sub.1 -C.sub.3 lower alkyl or C.sub.2 -C.sub.3 acyl and Z.sub.3 represents methyl or hydrogen with the proviso that Z.sub.1 and Z.sub.2 are not both hydrogen, and uses thereof in augmenting, enhancing or imparting aromas in and to perfume compositions, colognes, perfumed polymers and perfumed articles.Type: GrantFiled: April 25, 1995Date of Patent: August 13, 1996Assignee: International Flavors & Fragrances Inc.Inventors: Michael G. Monteleone, Richard A. Weiss, Mark D. Evans, Marie R. Hanna
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Patent number: 5532416Abstract: The present invention relates to novel 4-halo-2-fluoro-5-alkylbenzoyl compounds and their methods of manufacture. These compounds are useful for the preparation of agricultural chemicals and medicines, particularly as intermediates for an active class of aryl-haloalkylpyrazole and aryl alkylsulfonylpyrazole herbicides.Type: GrantFiled: July 20, 1994Date of Patent: July 2, 1996Assignee: Monsanto CompanyInventors: Bruce C. Hamper, Kindrick L. Leschinsky
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Patent number: 5475162Abstract: A process of effecting an acid catalyzed reaction wherein a reactant capable of undergoing an acid catalyzed reaction is contacted with an acid functionalized organically-bridged polysilsesquioxane catalyst where all of the acid functionality is covalently bonded to the organic portion of an organically-bridged polysilsesquioxane framework has been developed. The acid functionalized organically-bridged polysilsesquioxane is formed by polymerizing a monomer through sol-gel processing to form an organically-bridged polysilsesquioxane, reacting an acid group onto the organic portion of the organically-bridged polysilsesquioxane, and recovering the acid functionalized product. An embodiment of the invention is where the acid catalyzed reaction is the hydration of olefins, alkylation, acylation, isomerization, or aldol condensation/elimination.Type: GrantFiled: July 19, 1994Date of Patent: December 12, 1995Assignee: UOPInventors: Timothy A. Brandvold, Jennifer S. Holmgren, Thomas P. Malloy
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Patent number: 5466880Abstract: A novel multi-step process for preparing the (4S)-enantiomer of 4-(3,4 -dichlorophenyl)-3,4-1(2H)- naphthalenone in a highly-optically pure form is disclosed. The process involved starts from the known 4-(3,4-dichlorophenyl)-4-ketobutanoic acid and proceeds through such intermediates as (1) isopropyl or tert.- butyl 4-(3,4 -dichlorophenyl)-4-ketobutanoate, (2) isopropyl or tert.-butyl 4-(3,4-dichlorophenyl)-(4R)-hydroxybutanoate, (3) isopropyl or tert.-butyl 4-(3,4-dichlorophenyl-(4R)-sulfonyloxybutanoate, (4) isopropyl or tert.-butyl 4-(3,4-dichlorophenyl)-(4R)-phenylbutanoate to finally yield the desired (4S)-4-(3,4-dichlorophenyl)-3,4-dihydro -1(2H)-naphthalenone compound in a highly-optically pure form. The latter compound, which is a (4S)-enantiomer per se, has utility as an intermediate that ultimately leads to pure cis-(1S)(4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthal eneamine (sertraline), which is a known antidepressant agent. The aforementioned isopropyl and tert.Type: GrantFiled: June 9, 1994Date of Patent: November 14, 1995Assignee: Pfizer Inc.Inventor: George J. Quallich
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Patent number: 5434310Abstract: Acylbenzenes of the formula ##STR1## can be prepared by reaction of benzene with carboxylic acids of the formulaHOOC--R.sup.1 (II)where R.sup.1 has the meaning given in the text, using a molar ratio of benzene:carboxylic acid=1-50:1 at a temperature of 200.degree.-400.degree. C., a zeolite of the Pentasil type having an SiO.sub.2 /M.sup.2 O.sub.2 ratio of 15-500:1 being used as acid catalyst; in the latter formula, M.sup.2 is one element or more from the group comprising Al, B, Ga, In, Fe, Cr, V, As and Sb.Type: GrantFiled: January 12, 1994Date of Patent: July 18, 1995Assignee: Bayer AktiengesellschaftInventors: Helmut Waldmann, Manfred Hajek, Otto Immel, Lothar Puppe, Rudolf Braden
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Patent number: 5430015Abstract: A method of acetylating 1,2,3,4,-tetrahydro-1,1,2,4,4,7-hexamethylnapthalene (HMT) to produce 6-acetyl-1,2,3,4-tetrahydro-1,1,2,4,4,7-hexamethlnaphthalene (acetyl-HMT), comprises subjecting a mixture of 1,2,3,4-tetrahydro-1,1,2,4,4,7-hexamethlnaphthalene and or one or more substituted indanes or substituted acetylindanes to a Friedel-Crafts acetylation reaction in the presence of a saturated hydrocarbon solvent.Type: GrantFiled: March 16, 1993Date of Patent: July 4, 1995Assignee: Unilever Patent Holdings, BVInventors: Christopher P. Newman, Karen J. Rossiter, Terence L. Miller
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Patent number: 5360936Abstract: 1-Indanones of the formula IV or IVa ##STR1## in which R.sup.1 to R.sup.7 are preferably hydrogen or alkyl, or adjacent radicals R.sup.1 to R.sup.4 form a ring, are obtained in a one-step reaction by reacting a compound I ##STR2## with a compound of the formula II ##STR3## or with a compound of the formula (III) ##STR4## in anhydrous hydrogen fluoride and with boron trifluoride.Type: GrantFiled: September 10, 1993Date of Patent: November 1, 1994Assignee: Hoechst AktiengesellschaftInventors: Laurent Weisse, Heinz Strutz
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Patent number: 5347047Abstract: Acylaromatic compounds are prepared from aromatic compounds and carboxylic acids by reacting the starting compounds with phosgene in the presence of an aliphatic phosphine oxide or of an N,N-dialkylformamide and of an Fe(II), Fe(III) or Zn(II) compound.Type: GrantFiled: December 1, 1993Date of Patent: September 13, 1994Assignee: BASF AktiengesellschaftInventors: Wolfgang Siegel, Irene Troetsch-Schaller
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Patent number: 5329050Abstract: 1-Indanones of the formula IV or IVa ##STR1## in which R.sup.1 and R.sup.7 are preferably hydrogen or alkyl, or adjacent radicals R.sup.1 to R.sup.4 form a ring, are obtained in a one-step reaction by reacting a compound I ##STR2## with a compound of the formula II or a compound III ##STR3## in liquid hydrogen fluoride.Type: GrantFiled: April 27, 1993Date of Patent: July 12, 1994Assignee: Hoechst AktiengesellschaftInventors: Laurent Weisse, Jurgen Rohrmann, Frank Kuber, Heinz Strutz
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Patent number: 5329049Abstract: 1-Indanones of the formula III or IIIa ##STR1## in which R.sup.1 to R.sup.7 are preferably hydrogen or alkyl, or adjacent radicals R.sup.1 to R.sup.4 form a ring, are obtained in a one-step reaction by reacting a compound I ##STR2## with a compound of the formula II ##STR3## in liquid hydrogen fluoride.Type: GrantFiled: April 27, 1993Date of Patent: July 12, 1994Assignee: Hoechst AktiengesellschaftInventors: Laurent Weisse, Heinz Strutz
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Patent number: 5264633Abstract: A process for the preparation of 1,4-bis(4-hydroxybenzoyl)benzene of the formula (I) ##STR1## by rearranging diphenyl terephthalate of the formula (II) ##STR2## in about 3 to about 50 parts, relative to the diphenyl terephthalate, of an anhydrous organic solvent which is inert to the reactants, in the presence of about 30 to about 500 mol-% of a haloalkanesulfonic acid (catalyst) of the general formula (III) or (IV)Y(C.sub.n X.sub.2n)SO.sub.3 H (III)Y(C.sub.n F.sub.2n)SO.sub.3 H (IV)in which Y is a fluorine or hydrogen atom, and X is a fluorine and/or chlorine atom, with the proviso that at least one X is a fluorine atom, and n is an integer from 1 to 10, at temperatures of about 10.degree. to about 200.degree. C.Type: GrantFiled: April 29, 1992Date of Patent: November 23, 1993Assignee: Hoechst AktiengesellschaftInventors: Joachim Hackenbruch, Theodor Papenfuhs, Arnold Schneller
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Patent number: 5235068Abstract: Acylaromatic compounds ##STR1## (Q: aromatic compound residue; R: straight, branched or cyclic aliphatic group, aromatic group or araliphatic group) are prepared in high yield by a reaction, in the presence of a boron trifluoride complex catalyst, of an aromatic compound with ##STR2## (X: H, Cl, Br; Y: Cl, Br) or with RCOOH in the presence of (XYCHCO).sub.2 O.Type: GrantFiled: July 21, 1992Date of Patent: August 10, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Masayoshi Minai, Michitada Kondo, Yuji Ueda, Seiichi Kai, Takayuki Higashii
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Patent number: 5227529Abstract: A process for the acylation of naphthyl ethers of the formula ##STR1## using acylating agents of the formula R.sup.2 --CO--X to give acylated naphthyl ethers of the formula ##STR2## in which R.sup.1 and R.sup.2 independently of one another are C.sub.1 -- to C.sub.10 -alkyl, C.sub.2 -- to C.sub.10 -alkenyl or C.sub.3 - to C.sub.8 -cycloalkyl and R.sup.2 is additionally C.sub.6 - to C.sub.10 -aryl and X is Cl, Br, --OCOR.sup.2, OH or C.sub.1 - to C.sub.3 -alkoxy, comprises carrying out the reaction presence of zeolite catalysts which have the formula Z.Al.sub.2 O.sub.3.x SiO.sub.2 (III) in the anhydrous and template-free form, in which Z is M.sup.I.sub.2 O, M.sup.II O and/or (M.sup.III).sub.2 O.sub.3, in which M.sup.I is an alkali metal atom, ammonium or a hydrogen atom, M.sup.II is an alkaline earth metal atom and M.sup.Type: GrantFiled: September 14, 1992Date of Patent: July 13, 1993Assignee: Hoechst AktiengesellschaftInventors: Marita Neuber, Ernst I. Leupold
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Patent number: 5210313Abstract: A method for preparing isomerically pure 2,5-dichlorobenzophenones in good to high yields is provided. The invention comprises Friedel-Crafts aroylation of 1,4-dichlorobenzene using an aroyl halide or aromatic anhydride and at least one Lewis acid, the latter being present in an amount of at least about 1.1 mole per mole of aroyl halide or aromatic anhydride, preferably about 1.5 moles per mole of aroyl halide or aromatic anhydride and, more preferably, from about 2 to about 2.5 moles of Lewis acid per mole of aroyl halide or aromatic anhydride. Preferably, the molar ratio of 1,4-dichlorobenzene to aroyl halide ranges from about 1.2:1 to about 8:1.Type: GrantFiled: January 10, 1992Date of Patent: May 11, 1993Assignee: Maxdem IncorporatedInventors: Ying Wang, Mark S. Trimmer
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Patent number: 5210272Abstract: The preparation of magnesium benzyl fluoromalonate and other equivalent materials, the synthetic equivalents of the --CH.sub.2 F moiety, is described. Reaction between these reagents and the in situ-formed imidazolides of various carboxylic acids gives beta-keto-alpha-fluoroesters, which upon hydrogenation and spontaneous decarboxylation yields fluoromethyl ketones in excellent yields. The overall transformation from RCOOH to RCOCH.sub.2 F is thus illustrated.Type: GrantFiled: August 14, 1991Date of Patent: May 11, 1993Assignee: Prototek, Inc.Inventor: James T. Palmer
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Patent number: 5196607Abstract: A novel multi-step process for preparing the (4S)-enantiomer of 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone in a highly-optically pure form is disclosed. The process involves (1) first reacting 3,4-dichlorocinnamyl chloride with L-(-)-ephedrine in a chlorinated lower hydrocarbon solvent to form the corresponding chiral N-methyl-N-(.beta.-hydroxy-.beta.-phenylisopropyl)-3-(3,4-dichlorophenyl)p ropenoamide; (2) then subjecting the chiral .alpha.,.beta.-unsaturated amide formed in the first step to a Grignard reaction with phenyl magnesium chloride or bromide, followed by hydrolysis, to effect a conjugate addition of the phenyl group and the hydrogen element to the aforesaid .alpha.,.beta.-unsaturated propenoamide and so selectively form the corresponding chiral N-methyl-N-(.beta.-hydroxy-.beta.Type: GrantFiled: February 14, 1992Date of Patent: March 23, 1993Assignee: Pfizer Inc.Inventor: George J. Quallich
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Patent number: 5191133Abstract: The selective formation of 2-acetonaphthalene is achieved by acetylating naphthalene in the presence of liquid hydrogen fluoride. The 2-acetonaphthalene can be separated from the formed 1-acetonaphthalene isomer by successive hydrogenation of the isomer mixture and dehydration. The hydrogenation is selective to the 2-isomer while the 1-acetonaphthalene remains unreacted. Upon completion, 2-vinylnaphthalene can be distilled off from the unreacted 1-acetonaphthalene.Type: GrantFiled: May 22, 1991Date of Patent: March 2, 1993Assignee: Hoescht Celanese CorporationInventor: Henry C. Linstid, III
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Patent number: 5185469Abstract: A continuous process is disclosed for the acylation or alkylation of aromatic compounds in hydrogen fluoride. The aromatic compound is sufficiently insoluble in hydrogen fluoride that a two phase reaction medium forms. However, surprisingly, the product acylated or alkylated aromatic compound is soluble in hydrogen fluoride. The present invention particularly relates to use of a continuous, multi-stage process for carrying out the acylation or alkylation reaction. In the multi-stage process, the continuous phase can be either the hydrogen-fluoride rich phase or the aromatic compound-rich phase. The movement of the continuous phase relative to the non-continuous (dispersed) phase can be countercurrent or concurrent. The multi-stage process can be operated in a manner such that the aromatic compound feed to the reaction is entirely consumed or such that unreacted aromatic compound is recycled.Type: GrantFiled: August 23, 1991Date of Patent: February 9, 1993Assignee: Hoechst Celanese Corp.Inventors: Daniel D. Lindley, Timothy R. Ryan, Thomas A. Curtis, Edward M. De la Garza, Charles R. Hilton, Thomas M. Kenesson
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Patent number: 5162587Abstract: The present invention provides a novel compound represented as ##STR1## The present novel compound is prepared by reacting fluorine with pyridine-boron trifluoride and is useful as a fluorinating agent in the fluorination of organic compounds.Type: GrantFiled: October 18, 1991Date of Patent: November 10, 1992Assignee: Allied-Signal Inc.Inventors: Michael Van Der Puy, David Nalewajek, George A. Shia, William J. Wagner
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Patent number: 5144070Abstract: Disclosed is a process for the preparation of .alpha.-iodocarbonyl compounds such as .alpha.-iodocarboxylic acid anhydrides and .alpha.-iodoketones by the reaction of a carboxylic anhydride with molecular iodine. Hydrolysis of the .alpha.-iodocarboxylic acid anhydrides gives the corresponding .alpha.-iodocarboxylic acids.Type: GrantFiled: August 30, 1989Date of Patent: September 1, 1992Assignee: Eastman Kodak CompanyInventors: Joseph R. Zoeller, Michael R. Cushman, Regina M. Moncier
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Patent number: 5138098Abstract: A regioselective acylation process is provided for coverting a 2-methylnaphthalene compound to a 2-acetyl-6-methylnaphthalene compound. The process is conducted under liquid phase conditions in an acylation inert solvent using a complexing agent which is regiospecific for the beta position of naphthalene and which is a thermally stable nitrohydrocarbon compound. Preferred such agents are nitrobenzene, o-nitrotoluene, and mesitylene. Also provided is a novel method for producing a 2-acetyl-6-methylnaphthalene compound of relatively high purity from isomer mixtures by recrystallization from a hydrocarbon solvent, such as n-octane, isooctane, or n-nonane.Type: GrantFiled: March 14, 1991Date of Patent: August 11, 1992Assignee: Amoco CorporationInventors: Gary P. Hagen, Gregory E. Schmidt, John M. Weis, Thomas G. Smith
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Patent number: 5130448Abstract: 1-Aminoanthraquinone (1-AAQ) is synthesized by the condensation of 2-substituted benzoic acid and xylene to yield 2-substituted-dimethylbenzophenone, subsequent oxidation of the methyl groups, ring closure to form a 1-substituted anthraquinone carboxylic acid, replacement of the 1-substituent with ammonia, and decarboxylation.Type: GrantFiled: February 12, 1991Date of Patent: July 14, 1992Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Daniel A. Aguilar
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Patent number: 5126487Abstract: The subject invention relates to a process for the preparation of 2-alkyl-4-acyl-6-tert-butylphenol compound having the chemical structure: ##STR1## wherein -R is an aliphatic group having a terminally unsaturated moiety selected from --C.tbd.CH and --CH.dbd.C.dbd.CH.sub.2, and R' is selected from saturated, straight, branched or cyclic alkyl having from 1 to about 10 carbon atoms; the 2-alkyl-4-acyl-6-tert-butylphenol compound being produced in a reaction mixture comprising the corresponding 2-alkyl-6-tert-butylphenol: ##STR2## the corresponding carboxylic acid: RCOOH, and trifluoroacetic anhydride.Type: GrantFiled: March 26, 1991Date of Patent: June 30, 1992Assignee: The Procter & Gamble CompanyInventors: Thomas W. Gibson, Richard S. Echler
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Patent number: 5126489Abstract: Acylatable aromatic hydrocarbons may be acylated with a broad variety of carboxylic acid anhydrides in the presence of solid acid catalysts which replace conventional Friedel-Crafts catalysts to afford aromatic ketones in good yield and with high selectivity. Both aromatic and aliphatic carboxylic acid anhydrides may be used as the acylating agent, and solid acid catalysts such as the sulfated oxides of zirconia, pillared clays, and rare earth-exchanged pillared clays are found to be quite effective in the practice of this invention. The process may be practiced in a continuous mode, especially where excess aromatic compound is used as a reactant and is recycled from the product effluent to the reaction zone containing a bed of catalyst.Type: GrantFiled: May 6, 1991Date of Patent: June 30, 1992Assignee: UOPInventor: Paul R. Kurek
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Patent number: 5118862Abstract: Disclosed is a process for producing an .alpha.,.beta.-unsaturated carbonyl compound represented by the formula [II]: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each represents a hydrogen atom or a hydrocarbon residue and may be linear or may form a ring in optional combination thereof and total carbon atom number of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is 12 or less, which comprises contacting oxygen with an alkenyl compound represented by the formula [I]: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined above and X represents a trihydrocarbylsilyl group or an acyl group in the presence of a platinum group metal-supporting catalyst.Type: GrantFiled: August 27, 1990Date of Patent: June 2, 1992Assignee: Nippon Zeon Co., Ltd.Inventors: Toshihide Baba, Mitsuo Masai
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Patent number: 5118863Abstract: A process for producing an .alpha.,.beta.-unsaturated carbonyl compound represented by formula (II): ##STR1## which includes subjecting an alkenyl ester represented by formula (I): ##STR2## and an allyl type carbonic ester to catalytic reaction in the presence of a platinum group metal compound catalyst without the necessity of an organotin alkoxide. The subsequent addition of a phosphorus-containing compound, followed by heating, results in the decomposition and removal of unreacted allyl type carbonic ester and reaction by-product.Type: GrantFiled: September 5, 1991Date of Patent: June 2, 1992Assignee: Nippon Zeon Co., Ltd.Inventors: Kiyoshi Watanabe, Rikitaro Matsuoka
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Patent number: 5118860Abstract: In accordance with the present invention, aromatic ketones are prepared by the acylation of aromatic reactants using boron trifluoride as a catalyst and in a solvent medium comprising anhydrous liquid sulfur dioxide. The acylation proceeds in accordance with the equation I: ##STR1## wherein n ranges from 5 to 9, Ar is phenylene and n is 5, naphthalene and n is 7, or a bis phenylene radical having the structure: ##STR2## and n is 9; wherein Z is selected from the group consisting of a covalent carbon to carbon bond, O, S, SO.sub.2, C.dbd.O and C.sub.1 to C.sub.3 alkylene or alkylidene, X is selected from the group consisting of H, OH, halogen, C.sub.1 to C.sub.6 alkyl C.sub.1 to C.sub.6 alkoxy and combinations thereof, R is an alkyl group containing from 1 to about 16 carbon atoms and Y is selected from the group consisting of hydroxy, acyloxy and halogen.Type: GrantFiled: November 27, 1990Date of Patent: June 2, 1992Assignee: Hoechst Celanese CorporationInventor: Charlet R. Lindley
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Process for phenol alkylthiolation and its application to the synthesis of 4-acyl-2-alkylthiophenols
Patent number: 5113019Abstract: The invention relates to the preparation of alkylthiophenols by reaction of a dialkyl disulphide with a phenol.In the process according to the invention, the reaction is carried out in the presence of aluminum chloride or of ferric chloride in a solvent of the alkylbenzene type or, soley in the case of methylthiolation, in an excess of dimethyl disulphide.This process makes it possible, in particular to obtain, with a selectivity and in a yield which are excellent, 2-alkylthiophenols which may then be converted into 4-acyl-2-alkylthiophenols by means of a reaction at a temperature ranging from 40.degree. to 100.degree. C. with a complex BF.sub.3 :2RCOOH where R denotes an alkyl or propenyl radical, in a proportion of 10 to 15 moles of complex per mole of 2-alkylthiophenol.Type: GrantFiled: November 5, 1990Date of Patent: May 12, 1992Assignee: Societe Nationale Elf Aquitaine (Production)Inventors: Catherine Vottero, Yves Labat, Jean-Marie Poirier -
Patent number: 5107029Abstract: This invention concerns a process for preparing diketones and keto-acids by reacting a dicarboxylic acid and an aromatic compound in the presence of an alkylsulfonic acid such as methanesulfonic acid and an organic anhydride compound such as methanesulfonic anhydride or trifluoroacetic anhydride. The diketones and keto-acids can be used to prepare polyketones which are useful as molding plastics, coatings, films, fibers, and the like.Type: GrantFiled: July 23, 1990Date of Patent: April 21, 1992Assignee: Eastman Kodak CompanyInventors: Theodore R. Walker, Jr., Winston J. Jackson, Jr., Jean C. Fleischer
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Patent number: 5068448Abstract: A continuous process is provided for the production of 4'-isobutylacetophenone (4-IBAP) comprising feeding liquid hydrogen fluoride (HF) and an acetylating agent into an extractor-reactor to form a first, HF-rich phase containing the acetylating agent, feeding isobutylbenzene (IBB) to the extractor-reactor to form a second, IBB-rich phase which is contacted with said first, HF-rich phase in a manner such that the acetylating agent reacts with IBB to form 4-IBAP which is extracted into the first, HF-rich phase, and a light IBB-rich second phase containing the bulk of unreacted IBB, externally recycling said second, IBB-rich phase to the IBB feed point in combination with fresh IBB to make up for IBB consumed in the reaction and that and dissolved in the HF-rich phase, and withdrawing HF-rich phase containing 4-IBAP from the extractor-reactor.Type: GrantFiled: October 5, 1990Date of Patent: November 26, 1991Assignee: Hoechst Celanese CorporationInventors: Daniel D. Lindley, Thomas A. Curtis, Timothy R. Ryan, Edward M. de la Garza, Charles B. Hilton, Thomas M. Kenesson
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Patent number: 5041616Abstract: Disclosed is a process for the preparation of alkyl aryl ketones, cycloalkyl aryl ketones and diaryl ketones by contacting an aromatic compound with an aliphatic, cycloaliphatic or aromatic carboxylic acid in the presence of a catalytic amount of an organic sulfonic acid while removing the water of reaction as an azeotrope from the reaction mixture.Type: GrantFiled: August 29, 1990Date of Patent: August 20, 1991Assignee: Eastman Kodak CompanyInventor: Charles E. Sumner, Jr.
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Patent number: 5037854Abstract: A compound which has the biological action of inducing cell differentiation has general chemical formula (I), in which R.sub.1 is a straight or branched chain or cyclic alkyl or alkenyl group; R.sub.2 is an alkoxy or hydroxy group; R.sub.3 is a hydrogen or halogen atom; and, R.sub.4 is a halogen atom. Preferred values for the groups are R.sub.1 =C.sub.3 to C.sub.8 alkyl; R.sub.2 =methoxy; and, either or both of R.sub.3 and R.sub.4 =chlorine. The compounds: 1) 2,6-dihydroxy-3,5-dichloro-4-methoxy valerophenone; 2) 2,6-dihydroxy-3,5-dichloro-4-methoxy butyrophenone; and, 3) 2,6-dihydroxy-3-chloro-4-methoxy valerophenone are of particular interest.Type: GrantFiled: January 22, 1990Date of Patent: August 6, 1991Assignee: 3i Research Exploitation LimitedInventors: Howard R. Morris, Robert R. Kay, Mark S. Masento, Graham W. Taylor
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Patent number: 5015778Abstract: Hydroxy substituted arylophenones in general, and 4,4'-dihydroxybenzophenones in particular, are produced by catalytic oxidation of diaryl compounds containing hydroxy substituted diaryl moieties in a liquid medium. Oxidation occurs by contact of the diaryl compounds with an oxygen-containing gas in the presence of a solvent, base, a metal atom catalyst, and optionally, activated carbon. The arylophenones produced are useful as monomers in the production of epoxy and polycarbonate resins.Type: GrantFiled: December 18, 1989Date of Patent: May 14, 1991Assignee: The Dow Chemical CompanyInventors: Anthony P. Haag, E. W. Otterbacher
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Patent number: 5004832Abstract: Compounds are described of formula ##STR1## in which: Ar represents an aryl, possibly substituted;R represents a C.sub.1 -C.sub.4 alkyl;R' represents a hydroxyl, an alkoxy, an amino group possibly mono or di-alkyl substituted, or an O.sup.-- M.sup.+ group where M.sup.+ represents the cation of an alkaline metal;X represents a hydrogen, chlorine, bromine or iodine atom, a hydroxyl, or an acyloxy, alkylsulphonyloxy or arylsulphonyloxy group.The compounds of formula I can be easily transformed into alpha-arylalkanoic acids of formula ##STR2## in which Ar and R have the aforesaid meanings.Type: GrantFiled: February 6, 1989Date of Patent: April 2, 1991Assignee: Zambon S.p.A.Inventors: Graziano Castaldi, Claudio Giordano
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Patent number: 4990681Abstract: A method is provided for separating hydrogen fluoride (HF) from a mixture comprising HF complexed with an aromatic ketone in which the keto carbon atom is directly bonded to an aromatic ring carbon atom, e.g., 4-isobutylacetophenone, by adding a carboxylic acid anhydride, e.g., acetic anhydride, to the mixture while maintaining the mixture at conditions sufficient to sustain a reaction between the anhydride and the HF to form the corresponding acyl fluoride, e.g., acetyl fluoride, and carboxylic acid, e.g., acetic acid, and separating the acyl fluoride from the mixture. The method is conveniently carried out in a stripping column near the top of which the mixture comprising aromatic ketone and HF is fed and below which the anhydride is fed. Between these feed points, the uncomplexed HF is stripped from the mixture, while below the anhydride feed point or points, the anhydride reacts with the complexed HF to form the acyl fluoride which is stripped from the mixture, and the carboxylic acid.Type: GrantFiled: December 4, 1989Date of Patent: February 5, 1991Inventors: Thomas A. Curtis, Timothy R. Ryan, Daniel D. Lindley
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Patent number: 4983774Abstract: The preparation of ketones by reacting an acylating agent with an organo-manganous compound is catalyzed by a copper compound.Type: GrantFiled: December 16, 1988Date of Patent: January 8, 1991Assignee: Societe Nationale Elf AquitaineInventors: Gerard Cahiez, Blandine Laboue, Pierre Tozzolino
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Patent number: 4982005Abstract: Benzophenones are prepared by condensing benzoic acids and aromatics of the benzene series by means of boron trifluoride in nitrobenzene as reaction medium.Type: GrantFiled: August 23, 1989Date of Patent: January 1, 1991Assignee: BASF AktiengesellschaftInventors: Peter Neumann, Ulrich Eichenauer
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Patent number: 4973696Abstract: A stereoselective process is described for preparing optically active alpha,beta-disubstituted carbonyl compounds, comprising forming an acetal between an alpha,beta-unsaturated aldehyde or ketone and tartaric acid or a derivative thereof, halogenating the product thus obtained, and restoring the carbonyl compound.Type: GrantFiled: January 17, 1989Date of Patent: November 27, 1990Assignee: Zambon S.p.A.Inventors: Claudio Giordano, Graziano Castaldi, Silvia Cavicchioli, Francesco Minisci