Acyclic Hydrocarbyl Group Bonded Directly To The Benzene Ring Patents (Class 568/658)
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Patent number: 5344997Abstract: A fluorided silica-alumina catalyst, particularly one with a silica:alumina ratio in the range of 1:1-9:1 containing from 1 to 6 weight percent fluoride, is particularly effective in the liquid phase alkylation of benzene by linear olefins to produce linear alkyl benzenes at temperatures no greater than 140.degree. C. These catalysts also are effective in the liquid phase alkylation of alkylatable aromatics generally with a variety of alkylating agents, including olefins, alcohols, and alkyl halides.Type: GrantFiled: December 14, 1992Date of Patent: September 6, 1994Assignee: UOPInventor: Joseph A. Kocal
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Patent number: 5321167Abstract: An alkoxidation production low in alkylene oxide and 1,4-dioxane content is prepared by reacting an alkylphenol or fatty alcohol with an alkylene oxide in the presence of an alkali fatty alkoxide obtained by direct reaction of an alkali hydroxide with a fatty alcohol at elevated temperature.Type: GrantFiled: December 23, 1992Date of Patent: June 14, 1994Assignee: Huls AktiengesellschaftInventors: Egbert Schroer, Klaus Schulze, Ekkehard Wienhofer
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Patent number: 5302732Abstract: Silica-aluminas having a sodium content less than about 0.1 weight percent show increased stability when used as a catalyst for the alkylation of aromatic compounds. Where such silica-aluminas are used as the catalyst in detergent alkylation their increased stability permits continuous alkylation to be performed at lower temperatures, as a result of which the detergent alkylate product shows an incrementally higher linearity. Fluorided silica-aluminas having a sodium content of under 0.05 weight percent are particularly advantageous.Type: GrantFiled: September 14, 1992Date of Patent: April 12, 1994Assignee: UOPInventors: Karl Z. Steigleder, Christine M. Conway, David M. Baldwin, Diane C. Dierking
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Patent number: 5130435Abstract: Vinyl ethers of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are identical to or different from one another, each being hydrogen, straight-chain or branched alkyl or alkenyl of up to 12 carbon atoms, cycloalkyl or cycloalkylene of from 5 to 8 carbon atoms, aryl, alkylaryl, alkenylaryl, aralkyl and aralkenyl of from 6 to 16 carbon atoms, halogen-substituted aryl or heterocyclyl, and in addition the radicals R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3, together with the carbon atom to which they are bonded, can form a cycloalkane, cycloalkene or a heterocycle, and R.sup.4 is alkyl, alkylaryl or aralkyl, are prepared by eliminating an alcohol from an acetal/ketal of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.Type: GrantFiled: August 9, 1990Date of Patent: July 14, 1992Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
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Patent number: 5006534Abstract: Substituted benzyl ethers, benzyl thioethers, and benzylamines of the formula ##STR1## in which R.sup.1 and R.sup.2 are identical or different and represent hydrogen, alkyl, alkenyl, cycloalkyl, alkoxy, alkylthio, halogenoalkyl, sulphonylalkyl, halogenoalkoxy, halogenoalkylthio, aralkoxy, aralkylthio, halogen, nitro, cyano or hydroxyl, or represent a group of the formula ##STR2## wherein R.sup.4 and R.sup.5 are identical or different and represent hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, aryl or acyl,R.sup.3 represents a group of the formula ##STR3## in which R.sup.6 represents hydrogen, alkyl or acyl,R.sup.7 represents hydrogen or alkyl andn represents a number from 3 to 10,B represents --CH.sub.2 --X-- or --X--CH.sub.2 --,wherein X represents O, S or NR.sup.7,and wherein R.sup.7 has the abovementioned meaning and the group ##STR4## represents a benzo-fused heterocyclic system, A in the heterocyclic radical being 3-, 4- or 5-membered and containing nitrogen, oxygen and/or sulphur as hetero-atoms.Type: GrantFiled: January 30, 1989Date of Patent: April 9, 1991Assignee: Bayer AktiengesellschaftInventors: Klaus-Helmut Mohrs, Romanis Fruchtmann, Christian Kohlsdorfer
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Patent number: 4960884Abstract: Pesticidal mono-, di-, and tri-2-fluoroethyl ethers of the formula R.sup.1 R.sup.2.sub.m Ar(OCH.sub.2 CH.sub.2 F).sub.n, compositions thereof and their insecticidal, acaricidal and nematicidal uses are described and claimed.Type: GrantFiled: August 28, 1989Date of Patent: October 2, 1990Assignee: FMC CorporationInventors: David M. Roush, Donald A. Shaw, Michael L. Jones, Jun H. Chang
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Patent number: 4918242Abstract: A process for producing the optically pure (+)- or (-)-isomer of a phenyl- or substituted-phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.Type: GrantFiled: June 12, 1989Date of Patent: April 17, 1990Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 4902850Abstract: A method of purification for anethole which involves forming an aqueous emulsion of crude anethole and crystallizing anethole from the emulsion. The process provides a purified anethole having improved odor and taste.Type: GrantFiled: August 5, 1988Date of Patent: February 20, 1990Assignee: Arizona Chemical CompanyInventor: Curry B. Davis
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Patent number: 4898993Abstract: A process is described which permits to prepare substantially pure 2-tert-butyl-4-methoxyphenol, by reacting 4-bromo-2-tert-butylphenol with a methoxide in an organic solvent.The process permits to obtain a substantially pure 2-isomer, and avoids the need for the separation of the 2- and 3-isomers.Type: GrantFiled: January 13, 1988Date of Patent: February 6, 1990Assignee: Bromine Compounds LimitedInventors: Abram Becker, Nurit Kornberg, Berta Croitoru
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Patent number: 4846998Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 Iin whichR.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, in which one or two non-adjacent CH.sub.2 groups can also be replaced by O atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --A-- or --A--A.sup.4 --,A is a trans-1,4-cyclohexylene group which can be substituted in the 2-, 3-, 5- and/or 6-position one or more times by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group which each have 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, and which may also be substituted in the 1- and/or 4-position,A.sup.2, A.sup.3 and A.sup.Type: GrantFiled: November 21, 1986Date of Patent: July 11, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Ludwig Pohl, Bernhard Scheuble, Reinhard Hittich, Rudolf Eidenschink, Hans A. Kurmeier, Andreas Wachtler
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Patent number: 4814519Abstract: A process for the production of ethers from an olefin containing feedstock. The process includes two-stages for the production of ethers which comprises, in a first stage, isomerizing an olefin containing feedstock over a thermally stable layered metal oxide type catalyst having interspathic polymeric silica between the layers so as to produce iso-olefins and then, in a second stage, reacting the resultant iso-olefins with alcohols in the presence of an etherification catalyst so as to produce ethers from the iso-olegins.Type: GrantFiled: December 30, 1987Date of Patent: March 21, 1989Assignee: Mobil Oil CorporationInventors: Mohsen N. Harandi, Hartley Owen
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Patent number: 4757051Abstract: Novel 2-tert-butyl-4-methylcyclohexanol derivatives of the general formula I ##STR1## where R.sup.1 is alkyl of 1 to 3 carbon atoms or an acyl group ##STR2## where R.sup.2 is alkyl of 1 to 5 carbon atoms, and a process for their preparation, their use as scents, and scent compositions containing compounds of the formula I.Particularly interesting compounds are 2-tert-butyl-4-methylcyclohexyl acetate and propionate.Type: GrantFiled: August 11, 1987Date of Patent: July 12, 1988Assignee: BASF AktiengesellschaftInventors: Walter Gramlich, Werner Hoffman, Ludwig Schuster
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Patent number: 4710316Abstract: Compounds of the general formula (I) ##STR1## and compounds of the general formula (II) ##STR2## in which R.sup.1 represents --OH, --CH.sub.2 OH, --CH.sub.2 --OCH.sub.3, --CHOH--CH.sub.3, --CHO or --CH(OCH.sub.3).sub.2,R.sup.2 represents methyl or ethyl,R.sup.3 represents hydrogen or methyl, andX represents hydrogen or methyl, are disclosed.Processes for the manufacture of certain compounds of formula (I) and for those of formula (II) are also provided. The compounds are useful as perfume materials.Type: GrantFiled: August 13, 1986Date of Patent: December 1, 1987Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Walter Hafner, Peter Ritter, Helmut Gebauer, Marlies Regiert
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Patent number: 4704481Abstract: Benzylic and aromatic mercaptans are desulphurized by contacting the mercaptan with carbon monoxide at elevated temperatures in the presence of an aqueous hydrocarbon and a cobalt carbonyl catalyst.Type: GrantFiled: January 6, 1986Date of Patent: November 3, 1987Assignee: The British Petroleum Company p.l.c.Inventors: Howard Alper, David J. H. Smith
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Patent number: 4700005Abstract: Phenolic ethers are produced by reacting a phenol with a compound selected from an alkyl halide, an aryl halide, a dialkyl sulphate and a diaryl sulphate in the presence as catalyst of an amidine.Type: GrantFiled: June 6, 1986Date of Patent: October 13, 1987Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4675454Abstract: A process for etherifying phenols comprising reacting phenols at elevated temperature and pressure with a reactant selected from the group consisting of alcohol, ether and mixtures thereof in the presence of a catalyst comprising a sulfated oxide of a Group IB metal selected from the group consisting of Cu, Ag, Au and mixtures thereof on a support.Type: GrantFiled: March 10, 1986Date of Patent: June 23, 1987Assignee: Amoco CorporationInventor: Allen B. Mossman
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Patent number: 4675455Abstract: A process for etherifying phenols comprising reacting phenols at elevated temperature and pressure with a reactant selected from the group consisting of alcohol, ether and mixtures thereof in the presence of a catalyst comprising a sulfated oxide of a Group VIB metal selected from the group consisting of Cr, Mo, and mixtures thereof on a support.Type: GrantFiled: April 17, 1986Date of Patent: June 23, 1987Assignee: Amoco CorporationInventor: Allen B. Mossman
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Patent number: 4675456Abstract: A process for etherifying phenols comprising reacting phenols at elevated temperature and pressure with a reactant selected from the group consisting of alcohol, ether and mixtures thereof in the presence of a catalyst comprising a sulfated oxide of a lanthanide series metal selected from the group consisting of the lanthanide series metals and mixtures thereof on a support.Type: GrantFiled: April 17, 1986Date of Patent: June 23, 1987Assignee: Amoco CorporationInventor: Allen B. Mossman
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Patent number: 4650604Abstract: Perfume compositions and perfumed products characterized by a content of one or more fragrances which have the characteristic odor of vanilla and correspond to the formula ##STR1## wherein R.sub.1 or R.sub.2 represents a hydrogen atom and the other symbol an ethyl or propyl group and R.sub.3 represents a methyl or ethyl group.Type: GrantFiled: October 16, 1985Date of Patent: March 17, 1987Assignee: Naarden International N. V.Inventors: Nicolaas L. J. M. Broekhof, Antonius J. A. van der Weerdt
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Patent number: 4650910Abstract: Substituted styrenes are prepared by treatment on N-acyl-B-phenethylamines with bases and removal by distillation of the styrene which is formed during the reaction.Type: GrantFiled: March 4, 1986Date of Patent: March 17, 1987Assignee: Bayer AktiengesellschaftInventors: Karl-Wilhelm Henneke, Karlfried Wedemeyer
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Patent number: 4611084Abstract: A process for etherifying phenols comprising reacting phenols at elevated temperature and pressure with a reactant selected from the group consisting of alcohol, ether and mixtures thereof in the presence of a catalyst comprising a sulfated oxide of a Group VIIB metal selected from the group consisting of Mn, Re, and mixtures thereof on a support.Type: GrantFiled: November 25, 1985Date of Patent: September 9, 1986Assignee: Amoco CorporationInventor: Allen B. Mossman
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Patent number: 4562299Abstract: A process for the preparation of water-soluble vicinal diols by means of a direct catalytic hydroxylation of the corresponding olefines with H.sub.2 O.sub.2. An olefine possibly carrying functional groups inert under the reaction conditions, and whose corresponding vicinal diol is soluble in water, is made to react, under vigorous stirring, with H.sub.2 O.sub.2 at a temperature between 0.degree. and 120.degree. C. and at a pressure between 1 and 100 atmospheres, in a two-phase aqueous liquid/organic liquid system consisting or consisting essentially of an acid aqueous phase containing H.sub.2 O.sub.2 and of an organic phase containing (1) said olefine; (2) possibly a solvent immiscible with the aqueous phase; and (3) a catalyst of the formula:Q.sub.3 XW.sub.4 O.sub.24-2nwherein Q represents an onium (RR.sub.1 R.sub.2 R.sub.3 M).sup.+ cation, wherein M is chosen from among N, P, As and Sb, and R, R.sub.1, R.sub.2 and R.sub.Type: GrantFiled: December 12, 1984Date of Patent: December 31, 1985Assignee: Montedison S.p.A.Inventors: Carlo Venturello, Mario Gambaro
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Patent number: 4538002Abstract: There is disclosed a process for the production of alkylated hydroxyanisoles which consists of dehydrogenating para-isopropylphenol to para-isopropenylphenol which is then reacted with a methylating agent to yield para-isopropenylanisole which is then treated with acidic hydrogen peroxide to yield para-hydroxyanisole which is then treated with an alkylating agent to yield the alkylated hydroxyanisole. The process of this invention is especially useful for the synthesis of the food preservative butylated hydroxyanisole (BHA).Type: GrantFiled: September 10, 1984Date of Patent: August 27, 1985Assignee: The Goodyear Tire & Rubber CompanyInventors: Howard A. Colvin, Joel Muse, Jr., William S. Hollingshead
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Patent number: 4533758Abstract: Acid Phosphates are used, in either the gas or liquid phase, to catalyze the alkylation of phenols by an alcohol to selectively form alkyl aryl ethers.Type: GrantFiled: January 19, 1984Date of Patent: August 6, 1985Assignee: Air Products and Chemicals, Inc.Inventors: James E. Wells, Victoria Eskinazi
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Patent number: 4521635Abstract: Production of bis-(alpha-alkylbenzyl)ethers or substituted derivatives thereof by reaction at elevated temperature of the corresponding alpha alkylbenzyl alcohols in the presence of a mineral acid treated calcined alumina catalyst, quenching the catalyst with a basic compound and recovery of the desired ether by distillation following separation of the quenched catalyst, is disclosed. The alkyl methylbenzyl alcohol may be present as a component of an aromatic rich distill and product mixture derived from the ethyl benzene hydroperoxide epoxidation of an olefinically unsaturated compound.Type: GrantFiled: December 16, 1983Date of Patent: June 4, 1985Assignee: Atlantic Richfield CompanyInventor: Frank Stevens
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Patent number: 4501910Abstract: The invention concerns a process transforming an aldehyde into a corresponding alkene, of the type wherein the aldehyde is placed in the presence of a phosphoric reagent and a base in an organic solvent.The process consists in using an alcohol as the solvent and as a base a mineral base which in an aqueous medium evinces a basic strength equal to or less than that of the hydroxide ion, or a strongly basic organic base of the amine family, and in limiting the hydration rate of the reaction medium to a value at most of 10 moles of water per mole of aldehyde.Type: GrantFiled: October 12, 1982Date of Patent: February 26, 1985Assignee: Agrifurane, S.A.Inventors: Michel Delmas, Antoine Gaset, Yves le Bigot
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Patent number: 4450306Abstract: La.sub.2 (HPO.sub.4).sub.3, Sr(HSO.sub.4).sub.2 and Ba(HSO.sub.4).sub.2 are used, in either the gas or liquid phase, to catalyze the alkylation of phenols by alcohol to selectively form alkyl aryl ethers.Type: GrantFiled: November 8, 1982Date of Patent: May 22, 1984Assignee: Air Products and Chemicals, Inc.Inventor: Victoria Eskinazi
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Patent number: 4447652Abstract: Alkyl aryl ethers may be prepared in good yields by reacting a phenol with an olefin in the presence of an unmodified cationic exchange resin bearing sulfonic acid groups at low temperature. In another variation the ethers may be prepared by using as a catalyst the aforementioned resin where from about 10 to about 90 percent of the sulfonic acid groups are in the form of their alkali metal salts and the reaction temperature is greater than about 75.degree. C.Type: GrantFiled: May 21, 1982Date of Patent: May 8, 1984Assignee: UOP Inc.Inventor: Paul R. Kurek
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Patent number: 4400566Abstract: Organic halides are reduced to a dechlorinated products with a catalyst mixture consisting essentially of a nickel compound, a triarylphosphine and a halide ion, in the presence of reducing means for maintaining nickel in the zero valent state.Type: GrantFiled: March 24, 1982Date of Patent: August 23, 1983Assignee: Union Carbide CorporationInventor: Ismael Colon
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Patent number: 4347256Abstract: This invention relates to substituted isopentenyl phenyl compounds and their use as anti-juvenile hormones. The compounds have been found effective in the control of insects by inhibiting the actions of juvenile hormones. Such compounds act to induce precocious maturation of immature insects resulting in a reduction in the ecological impact of the insect. Additional effects which have been obtained include sterilization of mature insects. Based on previous research it is also believed these compounds will cause interruption of embryogenesis in insect eggs, the induction of diapause in insects and the prevention of sex pheromone secretion in insects.Type: GrantFiled: March 2, 1981Date of Patent: August 31, 1982Assignee: Cornell Research Foundation, Inc.Inventor: William S. Bowers
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Patent number: 4346040Abstract: The invention relates to a process for converting an aldehyde into a corresponding alkene and of the type wherein the aldehyde is placed in the presence of a phosphoric reagent and a base in solution in an organic aprotic solvent; the process comprising using a mineral base evincing in an aqueous medium a basic force less than or equal to that of the hydroxide ion or a strongly basic organic base of the nitrogen compounds family and adjusting the hydration rate of the reaction medium in such a manner that there are about 0.5 to 5 moles of water per mole of aldehyde.Type: GrantFiled: July 21, 1981Date of Patent: August 24, 1982Assignee: Agrifurane S.A.Inventors: Michel Delmas, Antoine Gaset, Yves Le Bigot
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Patent number: 4307253Abstract: Procecss for the preparation of alkyl aryl ethers by reacting phenols with aliphatic ethers in the presence of strongly acid cation exchangers.Type: GrantFiled: January 7, 1980Date of Patent: December 22, 1981Assignee: Bayer AktiengesellschaftInventors: Rainer Neumann, Hans-Helmut Schwarz, Dieter Nachtsheim
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Patent number: 4299996Abstract: Phenol compounds are O-alkylated with olefins in the presence of acid resin catalysts to give aryl alkyl ethers. In a preferred embodiment, the catalyst comprises perfluorosulfonic acid ion exchange resins.Type: GrantFiled: March 21, 1980Date of Patent: November 10, 1981Assignee: Phillips Petroleum Co.Inventor: Robert M. Parlman
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Patent number: 4263212Abstract: The present invention relates to a process for the preparation of aromatic or furyl substituted olefins, which comprises reacting an olefinic compound with an aromatic compound or furan compound in the presence of carbon monoxide by using a rhodium carbonyl complex as a catalyst to form a corresponding aromatic or furyl substituted olefin.Type: GrantFiled: February 14, 1980Date of Patent: April 21, 1981Assignee: Rikagaku KenkyushoInventors: Pangbu Hong, Hiroshi Yamazaki
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Patent number: 4192949Abstract: Phenol ethers are prepared by reacting phenols with dialkyl carbonates in the presence of tertiary amines and/or phosphines. The aralkyl aryl ethers and alkyl aryl ethers obtained are starting materials for the manufacture of dyes, crop protection agents and scents.Type: GrantFiled: June 15, 1978Date of Patent: March 11, 1980Assignee: BASF AktiengesellschaftInventors: Franz Merger, Friedrich Towae, Ludwig Schroff, deceased
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Patent number: 4163865Abstract: An improvement in a process for the preparation of a pinacol of the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and represent optionally substituted aliphatic, cycloaliphatic, araliphatic or an aromatic hydrocarbon radical by reducing a ketone of the formula ##STR2## wherein R.sup.1 and R.sup.2 have the abovementioned meanings with a base metal, the improvement comprising carrying out the reduction in the presence of an organic halogen compound and in the presence of a phosphoric acid amide, phosphoric acid ester and/or carboxylic acid amide.Type: GrantFiled: April 3, 1978Date of Patent: August 7, 1979Assignee: Bayer AktiengesellschaftInventors: Heinrich Wolfers, Hans Rudolph, Hans-Jurgen Rosenkranz
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Patent number: 4153810Abstract: Process for the preparation of alkyl aryl ethers by reacting aromatic hydroxy compounds with aliphatic alcohols in the presence of strongly acidic cation exchangers based on synthetic resins using the aromatic hydroxy compound in excess of the aliphatic alcohol.Type: GrantFiled: November 18, 1977Date of Patent: May 8, 1979Assignee: Haarmann & Reimer GmbHInventors: Rainer Neumann, Hans-Helmut Schwarz, Karl-Heinz Arnold
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Patent number: 4138411Abstract: Aromatic alkenyl compounds, for example, eugenol and safrole, are isomerized, for example to isoeugenol and isosafrole, by contact with a ruthenium or osmium catalyst.Type: GrantFiled: April 14, 1976Date of Patent: February 6, 1979Assignee: Rhone-Poulenc S. A.Inventor: Pierre Gandilhon