Preparing By Hydroxylation Of Benzene Ring Patents (Class 568/629)
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Patent number: 9630899Abstract: The present disclosure relates to an improved, environmentally friendly, process for producing compounds such as hydroquinone (benzene-1,4-diol) and its derivatives. The process can be carried out at ambient temperature and pressure using a recyclable copper catalyst and recyclable intermediate materials. The process generally entails reacting an aromatic compound such as benzene with hydrogen peroxide in the present of a pure elemental copper catalyst or a copper (I) salt catalyst to form oxidation product such as benzoquinone, and reducing the compound to hydroquinone or a hydroquinone derivative.Type: GrantFiled: October 26, 2015Date of Patent: April 25, 2017Assignee: Chang Chun Plastics Co. Ltd.Inventors: Chien Fu Huang, Yi Hung Chou
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Publication number: 20150045580Abstract: Selectively fluorinated molecules are important as materials, pharmaceuticals, and agrochemicals, but their synthesis by simple, mild, laboratory methods is challenging. We report a straightforward method for the cross-coupling of a difluoromethyl group with readily available reagents to form difluoromethylarenes. The reaction of electron-neutral, electronrich, and sterically hindered aryl and vinyl iodides with the combination of Cul, CsF and TMSCF2H leads to the formation of difluoromethylarenes in high yield with good functional group compatibility. This transformation is surprising, in part, because of the prior observation of the instability of CuCF2H.Type: ApplicationFiled: March 5, 2013Publication date: February 12, 2015Inventors: John Hartwig, Patrick Fier
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Patent number: 8791308Abstract: A process for the hydroxylation of phenols and of phenol ethers by hydrogen peroxide is described. More particularly a process for the hydroxylation of phenol by hydrogen peroxide is described. The described process can include hydroxylation of a phenol or of a phenol ether having at least one hydrogen atom at the ortho and para position of the hydroxyl group or of the ether group, by reaction of said phenol or phenol ether, with hydrogen peroxide, in the presence of an acid catalyst, wherein the reaction is carried out in the presence of an effective amount of a catalyst which is a mixture of at least two strong acids and wherein one of the acids is chosen from strong protonic acids and the other acid is chosen from superacids.Type: GrantFiled: March 30, 2010Date of Patent: July 29, 2014Assignee: Rhodia OperationsInventor: Laurent Garel
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Publication number: 20140073818Abstract: A method for hydroxylating phenols and phenol ethers using hydrogen peroxide and specifically, a method for hydroxylating phenol using hydrogen peroxide. The method for hydroxylating a phenolic substrate selected from a phenol or a phenol ether by reacting such phenolic substrate with hydrogen peroxide in the presence of an acid catalyst comprises the following steps, implemented consecutively or simultaneously: a first step consisting of mixing a phenolic substrate with a hydrogen peroxide solution under conditions in which the temperature is sufficient for the initial phenolic substrate to remain liquid and for minimizing the conversion rate of the hydrogen peroxide; a second step consisting of carrying out the phenolic substrate hydroxylation reaction under adiabatic conditions, the acid catalyst being added at the mixing stage and/or at the beginning of the hydroxylation reaction; and a third step, if necessary, consisting of recovering the hydroxylated product.Type: ApplicationFiled: May 15, 2012Publication date: March 13, 2014Applicant: RHODIA OPERATIONSInventors: Laurent Garel, Stephanie Normand, Pascal Pitiot, Jean-Christophe Bigouraux
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Publication number: 20130211102Abstract: The present invention relates to the scaled-up synthesis of biologically active compounds which display useful therapeutic activity in treating proliferative disorders. In particular the invention relates to process methods for the kilogram scale synthesis of a particular class of substituted benzofuran tubulin polymerisation inhibitors.Type: ApplicationFiled: July 15, 2011Publication date: August 15, 2013Applicant: BIONOMICS LIMITEDInventor: Bernard Luke Flynn
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Publication number: 20120035397Abstract: A process for the hydroxylation of phenols and of phenol ethers by hydrogen peroxide is described. More particularly a process for the hydroxylation of phenol by hydrogen peroxide is described. The described process can include hydroxylation of a phenol or of a phenol ether having at least one hydrogen atom at the ortho and para position of the hydroxyl group or of the ether group, by reaction of said phenol or phenol ether, with hydrogen peroxide, in the presence of an acid catalyst, wherein the reaction is carried out in the presence of an effective amount of a catalyst which is a mixture of at least two strong acids and wherein one of the acids is chosen from strong protonic acids and the other acid is chosen from superacids.Type: ApplicationFiled: March 30, 2010Publication date: February 9, 2012Applicant: RHODIA OPERATIONSInventor: Laurent Garel
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Publication number: 20100286451Abstract: The present invention relates to a process for producing a 2-fluoro-6-halophenol as an intermediate; a process for producing a 2-alkoxy-3-fluorophenol and further a 1,2-dialkoxy-3-fluorobenzene from the 2-fluoro-6-halophenol; a second process for producing a 1,2-dialkoxy-3-fluorobenzene from the 2-fluoro-6-halophenol; and a 2-alkoxy-3-fluorophenol. The 2-fluoro-6-halophenol can be obtained using a 2-fluorophenol as a starting material and through a sulfonation reaction, a halogenation reaction, and a deprotection reaction. The 2-fluoro-6-halophenol is alkyl-etherified, and subsequently the halogen atom is converted into a hydroxyl group to obtain the 2-alkoxy-3-fluorophenol, which is further alkyl-etherified to thereby obtain the 1,2-dialkoxy-3-fluorobenzene. Alternatively, a 1,2-dialkoxy-3-fluorobenzene is also obtained by converting the halogen atom of the 2-fluoro-6-halophenol into a hydroxyl group to thereby form 3-fluorocatechol and subsequently alkyl-etherifying two hydroxyl groups thereof.Type: ApplicationFiled: July 14, 2010Publication date: November 11, 2010Inventors: Mingjian Qiu, Wei Zhang, Zhaohui Chen, Chunshan Zhang, Yali Zhang
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Patent number: 7828991Abstract: This invention relates to novel polyether polyols which are prepared by alkoxylation of renewable resource materials, and particularly cashew nutshell liquid (CNSL), and to a process for the preparation of these novel polyether polyols. This invention also relates to flexible polyurethane foams prepared from these long chain polyether polyols, and to a process for the production of these flexible polyurethane foams.Type: GrantFiled: December 8, 2006Date of Patent: November 9, 2010Assignee: Bayer MaterialScience LLCInventors: Jack R. Reese, Micah N. Moore, Don S. Wardius, Stanley L. Hager
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Patent number: 7786330Abstract: The present invention relates to a process for producing a 2-fluoro-6-halophenol as an intermediate; a process for producing a 2-alkoxy-3-fluorophenol and further a 1,2-dialkoxy-3-fluorobenzene from the 2-fluoro-6-halophenol; a second process for producing a 1,2-dialkoxy-3-fluorobenzene from the 2-fluoro-6-halophenol; and a 2-alkoxy-3-fluorophenol. The 2-fluoro-6-halophenol can be obtained using a 2-fluorophenol as a starting material and through a sulfonation reaction, a halogenation reaction, and a deprotection reaction. The 2-fluoro-6-halophenol is alkyl-etherified, and subsequently the halogen atom is converted into a hydroxyl group to obtain the 2-alkoxy-3-fluorophenol, which is further alkyl-etherified to thereby obtain the 1,2-dialkoxy-3-fluorobenzene. Alternatively, a 1,2-dialkoxy-3-fluorobenzene is also obtained by converting the halogen atom of the 2-fluoro-6-halophenol into a hydroxyl group to thereby form 3-fluorocatechol and subsequently alkyl-etherifying two hydroxyl groups thereof.Type: GrantFiled: February 24, 2009Date of Patent: August 31, 2010Assignees: Asahi Glass Company, Limited, Charna Chemicals, Ltd.Inventors: Mingjian Qiu, Wei Zhang, Zhaohui Chen, Chunshan Zhang, Yali Zhang
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Patent number: 7781622Abstract: The present invention provides a process for direct hydroxylation of aromatic hydrocarbons like benzene to phenol, toluene to cresols and anisole to methoxy phenols by using hydrogen peroxide as environmentally benign oxidant in polar solvent like acetonitrile using vanadium phthalocyanine or its derivative as a catalyst, at a temperature in the range of 25-100° C.Type: GrantFiled: October 30, 2008Date of Patent: August 24, 2010Assignee: Council of Scientific & Industrial ResearchInventors: Suman Lata Jain, Jomy K. Joseph, Sweety Singhal, Bir Sain, Ragunathan Sivakumaran, Basant Kumar
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Patent number: 7625499Abstract: The present invention provides a conductive liquid-crystal material having features including that, for example, excellent conductivity is exhibited at a low threshold voltage of about 5 V even in a room temperature range, the value of resistance varies with an applied voltage, the current density rises sharply at a voltage of about 5 V, and an excellent charge mobility is exhibited, as well as a process for producing the conductive liquid-crystal material, a liquid-crystal composition which is used for the conductive liquid-crystal material, a liquid-crystal semiconductor element, and an information recording medium.Type: GrantFiled: November 30, 2005Date of Patent: December 1, 2009Assignee: Nippon Chemical Industrial Co., Ltd.Inventor: Yuichiro Haramoto
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Patent number: 7482494Abstract: The present invention provides a benzene derivative having a long, linear conjugated structure, the benzene derivative being capable of exhibiting a satisfactory ability to transport charge without photoexcitation, a process for producing the benzene derivative, and a liquid-crystal material and a charge-transport material containing the benzene derivative having a long, linear conjugated structure. That is, a benzene derivative having a long, linear conjugated structure represented by general formula (1): (wherein R1 represents a methyl group or a hydrogen atom, A represents an alkylene group, —CO—O—(CH2)n—, —C6H4—CH2—, or —CO—).Type: GrantFiled: March 22, 2004Date of Patent: January 27, 2009Assignee: Nippon Chemical Industrial Co., Ltd.Inventor: Yuichiro Haramoto
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Patent number: 7414157Abstract: The present invention pertains to a process for preparing a compound of Formula I that is achiral, racemic or enantiomerically enriched at the hydroxylation center indicated by comprising contacting a compound of Formula II with an oxidant selected from oxygen, hydrogen peroxide, peracids or alkyl hydroperoxides in the presence of a zirconium complex, wherein R1, R2 and R3 are as defined in the disclosure. This invention also pertains to zirconium complexes useful in this procedure comprising zirconium and a ligand of Formula III or its enantiomer wherein J, R6 and n are as defined in the disclosure. This invention further pertains to a compound of Formula III or its enantiomer.Type: GrantFiled: June 6, 2002Date of Patent: August 19, 2008Assignee: E. I. du Pont de Nemours and CompanyInventor: Albert Loren Casalnuovo
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Patent number: 7393465Abstract: A process for preparing hydrophobic polyols that includes reacting A) a mixture having an OH content of from 180 to 300 mg KOH/g, a viscosity at 23° C. of from 5000 to 20 000 mPas and an OH functionality of from 2.8 to 4.5 including from 5 to 20 wt. % of 3-pentadecadienylphenol, from 5 to 10 wt. % of 3-pentadecadienyl-recorcinol and from 1 to 5 wt. % of 2-methyl 3-pentadecadienylrecorcinol; with B) alkylene oxides (AO) with addition of the AO monomers onto the AO-reactive groups of component A); the ratio of the amounts of A) to B) being from 1:9 to 9:1; where the hydrophobic polyols have an OH number of from 140 to 220 mg KOH/g and a viscosity at 23° C. of from 1000 to 4000 mPas. The hydrophobic polyols can be used in polyurethane systems, in coatings, adhesive bonds, sealants or moulding compounds, which can be used to coat substrates.Type: GrantFiled: February 24, 2005Date of Patent: July 1, 2008Assignee: Bayer MaterialScience AGInventors: Meike Niesten, Jack Reese, Joachim Simon, Gerhard Ruttmann
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Patent number: 6977236Abstract: The present invention relates to a process for the preparation of a double metal cyanide (DMC) catalyst, which process involves: (a) combining an aqueous solution of metal salt with an aqueous solution of a metal cyanide salt and reacting these solutions; and (b) recovering the DMC catalyst from the reaction mixture, in which process the DMC catalyst is prepared in the presence of from 0.03 to 0.4 mole of alkaline metal compound, based on amount of metal salt. Further, the present invention relates to DMC catalyst obtainable by such process, to DMC catalyst prepared from a metal salt and a metal cyanide salt in which the molar ratio of metal derived from the metal salt to metal derived from the metal cyanide salt is at least 2.25 and to a process for polymerization of alkylene oxides which process involves reacting initiator with alkylene oxide in the presence of at most 15 ppm of DMC catalyst.Type: GrantFiled: February 17, 2004Date of Patent: December 20, 2005Assignee: Shell Oil CompanyInventors: Michiel Barend Eleveld, Robert Adrianus Wilhelmus Grotenbreg, Ronald van Kempen
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Patent number: 6765079Abstract: Novel cross linked polymer films prepared from poly4-[(4-cardanylazo]benzoic acid and poly4-[(4-acryloylcardanylazo]benzoic acid are disclosed. The invention also relates to novel monomers 4-[(4-cardanylazo] benzoic acid and 4-[(4-acryloylcardanylazo] benzoic acid and polymers thereof as well processes for the preparation thereof.Type: GrantFiled: March 24, 2003Date of Patent: July 20, 2004Assignee: Council of Scientific and Industrial ResearchInventors: Muthusamy Saminathan, Chennakkattu Krishna Sadasivan Pillai
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Patent number: 6756512Abstract: The invention relates to a novel process for preparing 2-alkyl-3-chlorophenols.Type: GrantFiled: October 30, 2002Date of Patent: June 29, 2004Assignee: Bayer AktiengesellschaftInventors: Walter Hübsch, Reinhard Lantzsch, Thorsten Müh, Holger Weintritt
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Patent number: 6479711Abstract: A process for producing an aromatic hydroxy compound having hydroxyl group at the para-position with respect to a hydroxy or an alkoxy substituent group present in the aromatic ring at a high yield and at a high selectivity, using a novel and useful hydroxylation catalyst which can afford to introduce hydroxyl group directly into aromatic ring at the para-position with respect to a hydroxy or an alkoxy substituent group, by reacting at least one compound selected from the group consisting of phenols, alkoxybenzenes and derivatives of them with hydrogen peroxide in the presence of the catalyst, wherein the hydroxylation catalyst is constituted of an oleophilized crystalline titanosilicate.Type: GrantFiled: April 28, 2000Date of Patent: November 12, 2002Assignee: Mitsui Chemicals, Inc.Inventors: Toshihiro Takai, Kazuaki Matsui
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Publication number: 20010039365Abstract: A method and composition are disclosed for the hydroxylation of aromatic substrates in the presence of oxygen, hydrogen, and a catalyst. In a preferred embodiment, benzene is oxidized to phenol in the presence of oxygen, a vanadium catalyst, and hydrogen. The method is economical, safe, and amenable to commercial scale-up.Type: ApplicationFiled: January 16, 2001Publication date: November 8, 2001Inventor: Terence Michael Barnhart
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Patent number: 6229054Abstract: The present invention comprises a process for the hydroxyalkylation of cardanol with cyclic organic carbonates in the presence of organic or inorganic catalysts and a novel composition of matter produced by that process. The unique molecular structure of cardanol allows the use of a variety of organic or inorganic basic catalysts, including triethylamine, imidazol, sodium hydroxide and sodium carbonate, in the hydroxyalkylation reaction without forming quantities of undesirable side-products. According to this invention, the final product, monohydroxyalkylcardanyl ether, can be obtained with high yield and high purity. The product has a light color and its color stability is enhanced by replacing the phenol's hydroxyl group with a more stable hydroxyalkoxyl group.Type: GrantFiled: December 9, 1999Date of Patent: May 8, 2001Assignee: Cardolite CorporationInventors: Zhisheng Dai, Meng J. Chen
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Patent number: 6156939Abstract: The invention relates to a process for the hydroxylation of aromatic hydrocarbons by direct oxidation with hydrogen peroxide. The process is carried out in the presence of a catalyst comprising:iron, administered as inorganic salt;iron ligand, consisting of carboxylic acids of ether-aromatic compounds containing nitrogen, in particular pyrazin-2-carboxylic acid and derivatives;acidifying agent, especially trifluoracetic acid, and a solvent system comprising an organic phase consisting of a substrate and acetonitrile and an aqueous phase containing the catalyst and hydrogen peroxide.Type: GrantFiled: April 4, 2000Date of Patent: December 5, 2000Assignee: Enichem S.p.A.Inventors: Rodolfo Vignola, Ezio Battistel, Daniele Bianchi, Rossella Bortolo, Roberto Tassinari
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Patent number: 5811592Abstract: Described are compounds defined according to the structure: ##STR1## wherein Z represents meta or para cyclohexylene or meta or para phenylene and wherein R.sub.1 and R.sub.2 are the same or different methyl or hydrogen; and wherein R.sub.3 represents C.sub.1 -C.sub.3 alkyl; and wherein the moiety: ##STR2## is ortho with respect to R.sub.2 and para or meta with respect to the moiety: ##STR3## with the proviso that the sum of the number of carbon atoms in R.sub.1, R.sub.2 and R.sub.3 is 3 or 4; and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles and hair preparations; as well as processes for preparing alkyl-substituted-C.sub.1 -C.sub.3 alkoxy-C.sub.6 -cycloaliphatic compounds.Type: GrantFiled: November 21, 1996Date of Patent: September 22, 1998Assignee: International Flavors & Fragrances Inc.Inventors: Michael G. Monteleone, Richard A. Weiss, Marc D. Evans, Marie R. Hanna
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Patent number: 5786519Abstract: An improved process is provided for the preparation of a mixture of guaiacol and p-methoxy phenol which comprises reacting anisole with hydrogen peroxide in the presence of a solid catalyst containing an organotransition metal complex wherein some or all of the hydrogen atoms of the said organotransition metal complex have been substituted by one or more electron withdrawing groups, and isolating the mixture of guaiacol and p-methoxy phenol formed.Type: GrantFiled: February 16, 1996Date of Patent: July 28, 1998Assignee: Council of Scientific & Industrial ResearchInventors: Pramod Prabhakar Moghe, Paul Ratnasamy, Robert Raja, Ashwini Vinayak Pol, Madhav Gopal Kotasthane, Prakash Kondiba Bahirat
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Patent number: 5688975Abstract: Molecular sieve compositions have been synthesized which are resistant to the loss of framework atoms. Specifically, the molecular sieves of the invention have the empirical formulamA: (M.sub.w Al.sub.x Si.sub.y)O.sub.2where A is at least one rare earth metal, M is chromium or titanium and "m", "w", "x" and "y" are the mole fractions of A, M, Al and Si respectively. Applicants have discovered that the rare earth metals prevent loss of chromium and titanium from the framework and degradation of the molecular sieve. Along with the composition, a process for preparing the composition and processes using the composition are disclosed and claimed.Type: GrantFiled: April 10, 1996Date of Patent: November 18, 1997Assignee: UOPInventors: Vinayan Nair, Deng-Yang Jan, Robert Lyle Patton, Ben A. Wilson, Donald F. Best
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Patent number: 5658951Abstract: Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes alkoxy substituents including a dialkylaminoalkoxy group, an unsubstituted piperazine alkoxy group, a substituted piperazine alkoxy group, an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group, and which may have one or two alkyl groups bonded to the cyclopropane. The compounds are useful as antiestrogens and anti-tumor agents.Type: GrantFiled: June 7, 1995Date of Patent: August 19, 1997Assignee: Research Corporation TechnologiesInventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
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Patent number: 5658927Abstract: Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes alkoxy substituents including a dialkylaminoalkoxy group, an unsubstituted piperazine alkoxy group, a substituted piperazine alkoxy group, an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group, and which may have one or two alkyl groups bonded to the cyclopropane. The compounds are useful as antiestrogens and anti-tumor agents.Type: GrantFiled: June 7, 1995Date of Patent: August 19, 1997Assignee: Research Corporation TechnologiesInventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
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Patent number: 5602283Abstract: A multistage process of preparing N-alkyl-3,4-dialkyl-2,6-dinitroanilines starts from 3,4-dialkyl phenol and goes through the stages of 3,4-dialkyl-2,6-dinitrophenol and 3,4-dialkyl-2,6-ditro alkoxybenzene, wherein the latter are new compounds.Type: GrantFiled: May 23, 1995Date of Patent: February 11, 1997Assignee: Agan Chemical Manufacturers Ltd.Inventor: Morris Sarel
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Patent number: 5416235Abstract: A process for the preparation of aromatic compounds of the general formula I,Ar--X Iin which Ar represents an optionally substituted aryl group and X represents a group OH, Cl, Br or CN, by reaction of an aryl diazoniumsalt of the formula II,Ar--N.dbd.N.sup.+ Y.sup.- IIin which Ar is as defined above and Y represents a suitable counterion, with water, hydrogen chloride or a salt thereof, hydrogen bromide or a salt thereof, or a cyanide in the presence of a copper(I)salt, characterized in that the copper(I)salt is a copper(I)salt derived from an hydroxy carboxylic acid.Type: GrantFiled: November 1, 1993Date of Patent: May 16, 1995Assignee: Octel Chemicals LimitedInventors: Bruce C. Gilbert, Peter Hanson, Jason R. Jones, Allan W. Timms
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Patent number: 5414153Abstract: Phenolic compounds, e.g., the phenols and phenol ethers, are selectively hydroxylated whereby the amounts of the final product para isomer are enhanced, for example in favor of hydroquinone versus pyrocatechol in the event of the hydroxylation of phenol, by reacting such phenolic compounds with hydrogen peroxide, advantageously in a polar, aprotic, organic solvent reaction medium, in the presence of a catalytically effective amount of a sulfonated polymer and a cocatalytically effective amount of an aromatic ketone compound.Type: GrantFiled: April 5, 1993Date of Patent: May 9, 1995Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Dominique Laucher
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Patent number: 5360938Abstract: This invention relates to asymmetric syntheses in which a prochiral or chiral compound is contacted in the presence of an optically active metal-ligand complex catalyst to produce an optically active product.Type: GrantFiled: July 16, 1992Date of Patent: November 1, 1994Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: James E. Babin, Gregory T. Whiteker
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Patent number: 5254746Abstract: The phenols and phenol ethers are hydroxylated by reaction with hydrogen peroxide in the presence of a catalytically effective amount of a titanozeosilite, advantageously a silicon oxide/titanium oxide MFI zeolite having the general formula:SI.sub.(96-x), Ti.sub.x O.sub.192.Type: GrantFiled: August 19, 1992Date of Patent: October 19, 1993Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Jean-Michel Popa, Michel Gubelmann
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Patent number: 5245086Abstract: The phenols/phenol ethers are hydroxylated by reaction with hydrogen peroxide, in the presence of a catalytically effective amount of (a) at least one alkali metal or alkaline earth metal salt of a protonic acid having a pKa in water of less than -0.1 and (b) a free protonic acid.Type: GrantFiled: December 5, 1990Date of Patent: September 14, 1993Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Dominique Laucher
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Patent number: 5233097Abstract: Certain crystalline titanoaluminosilicate molecular sieve compositions having titanium, aluminum, and silicon present as framework tetrahedral oxide units are particularly effective in hydroxylating the aromatic nucleus of aromatic compounds using hydrogen peroxide, even where the hydrogen peroxide is used at concentrations of 10 weight percent or less. The variant where the exchangeable hydrogens of the titanoaluminosilicate are replaced by an alkali or alkaline earth metal cation is particularly favored because of the concomitant increase in selectivity. Excellent utilization of hydrogen peroxide often is observed, even when the hydroxylation is effected at temperatures under about 60.degree. C.Type: GrantFiled: October 15, 1992Date of Patent: August 3, 1993Assignee: UOPInventors: Laszlo T. Nemeth, Eric M. Hyatt, Thomas P. Malloy
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Patent number: 5160496Abstract: The phenols and phenol ethers are economically and efficiently hydroxylated using hydrogen peroxide, in the presence of a catalytically effective amount of a bridged clay, e.g., a zeolite or smectite.Type: GrantFiled: July 16, 1990Date of Patent: November 3, 1992Assignee: Rhone-Poulenc ChimieInventors: Michel Constantini, Jean-Michel Popa
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Patent number: 5149888Abstract: The phenols and phenol ethers, e.g., phenol itself, are effectively hydroxylated by reacting hydrogen peroxide therewith, in the presence of a catalytically effective amount of titanium dioxide.Type: GrantFiled: February 28, 1990Date of Patent: September 22, 1992Assignee: Rone-Poulenc ChimieInventors: Michel Costantini, Eric Garcin, Michel Gubelmann, Jean-Michel Popa
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Patent number: 4954653Abstract: The invention discloses a catalyst on the basis of silicon and titanium having the form of microspheres and constituted by oligomeric silica and by titanium-silica-lite crystals having an oligomeric silica/titanium-silicalite molar ratio comprised within the range of from 0.05 to 0.11, wherein the crystals of titanium-silicalite are encaged by means of Si-O-Si bridges.Type: GrantFiled: June 7, 1989Date of Patent: September 4, 1990Assignee: Enichem Sintesi S.p.A.Inventors: Giuseppe Bellussi, Franco Buonomo, Antonio Esposito, Mario Clerici, Ugo Romano, Bruno Notari
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Patent number: 4814521Abstract: Disclosed herein is a process for producing 2,6-dihydroxynaphthalene which comprises oxidizing 2,6-di(2-hydroxy-2-propyl)naphthalene in acetonitrile, 1,4-dioxane or a mixture thereof with hydrogen peroxide in the presence of an inorganic acid or a solid acid at a temperture in the range of room temperature to the boiling point of the solution of the 2,6-di(2-hydroxy-2-propyl)naphthalene in acetonitrile or 1,4-dioxane, the acetonitrile, 1,4-dioxane or a mixture thereof being used in an amount of 3 to 30 ml to one gram of the 2,6-di(2-hydroxy-2-propyl)naphthalene.Type: GrantFiled: August 26, 1987Date of Patent: March 21, 1989Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Takayuki Tanonaka, Takashi Yamauchi, Hiroyuki Enari, Yutaka Konai
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Patent number: 4551562Abstract: The nuclear hydroxylation of phenol with organic solutions of hydrogen peroxide in the presence of a catalyst is carried out in improved manner by employing both (1) a special, practically water free solution of hydrogen peroxide in an organic solvent which does not form an azeotrope with water or whose highest azeotrope with water, boil near or above the boiling point of hydrogen peroxide, and (2) employing as a catalyst XO.sub.2 where X is sulfur, selenium, or tellurium. Besides increasing the yield and the ability to carry out the reaction in a simpler manner when selenium dioxide is employed as a catalyst, there can also be controlled the ortho-para ratio, respectively, the ortho-ortho ratio of the product.Type: GrantFiled: March 13, 1984Date of Patent: November 5, 1985Assignee: Degussa AktiengesellschaftInventors: Karlheinz Drauz, Axel Kleemann
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Patent number: 4533766Abstract: The known nuclear hydroxylation of substituted phenols or phenol ethers with organic solutions of hydrogen peroxide in the presence of a catalyst is carried out in improved manner by employing both (1) a special, practically water free solution of hydrogen peroxide in an organic solvent which forms an azeotrope with water, which azeotrope boils below the boiling point of hydrogen peroxide, and (2) sulfur dioxide as a catalyst. Through this, the nuclear hydroxylation is substantially simpler than previously; difficult separations, e.g., from water-phenol, or the separation and recovery of the catalyst are eliminated. Besides, the yields are increased.Type: GrantFiled: March 8, 1984Date of Patent: August 6, 1985Assignee: Degussa AktiengesellschaftInventors: Karlheinz Drauz, Axel Kleemann
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Patent number: 4422955Abstract: The invention relates to a process for substituting for a halogen atom attached to the nuclear carbon atom of an aromatic ring, a substituent of the formula --O--R wherein R represents alkyl, alkenyl, alkynyl or benzyl, which process comprises reacting the halogen-substituted aromatic compound with an alcoholate of the formula M.sup.n+ [O--R].sub.n.sup..crclbar. wherein M is an alkali metal atom or alkaline earth metal atom, n is the valency of M, and R is as defined above, in the presence of an active catalyst mixture comprising (i) a formic acid ester of an organic alcohol having the formula R.sup.2 --O--CO--H wherein R.sup.2 is as defined for R above; and (ii) a cuprous salt; in a liquid medium which is a solvent for the catalyst mixture and in which the halogen-substituted aromatic compound is at least partially soluble, under substantially anhydrous conditions and a non-oxidizing atmosphere. The invention further relates to a catalyst used in the above process.Type: GrantFiled: December 4, 1981Date of Patent: December 27, 1983Assignee: Sterling Drug Inc.Inventor: Robert J. Bryant
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Patent number: 4301307Abstract: Aromatic hydrocarbons and particularly phenols and phenol ethers can be hydroxylated by reacting the aromatic compound with hydrogen peroxide in a reaction medium comprising trifluoromethanesulfonic acid. High yields of hydroxylated aromatic compounds are obtained by this process which avoids the use of extremely corrosive and difficult to handle agents. Phenol is hydroxylated predominantly to hydroquinone by this process.Type: GrantFiled: December 20, 1979Date of Patent: November 17, 1981Assignee: Rhone-Poulenc IndustriesInventor: Michel Jouffret
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Patent number: 4174460Abstract: A process for the hydroxylation of phenols and phenol ethers in the nucleus with hydrogen peroxide wherein a phenol or a phenol ether is reacted at the start of the reaction with substantially anhydrous hydrogen peroxide and wherein the reaction is carried out in the presence of a strong acid.Type: GrantFiled: March 31, 1977Date of Patent: November 13, 1979Assignee: Bayer AktiengesellschaftInventors: Hermann Seifert, Helmut Waldman, Wulf Schwerdtel, Wolfgang Swodenk