Guaiacol Per Se Or Salt Thereof Patents (Class 568/653)
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Patent number: 8993809Abstract: A process for isolating at least one target compound, such as manool, geranyl linalool, ethyl guaiacol, eugenol, veratraldehyde, squalene, terpin, cholesterol, beta-sitosterol, campesterol, stigmasterol, stigmastenol and dehydroabietic acid, from biomass, the process including steps of: obtaining a condensate from a recovery evaporator, a reverse osmosis retentate of a condensate of a pulp and paper mill, or both, the condensate, retentate or both being substantially free of higher molecular weight (approximately >1000 Da) cellulose and/or lignin and/or lignin-derived material; optionally pH adjusting and filtering the condensate to collect insoluble material; extracting the condensate, the collected insoluble material, or both, with solid phase extraction (SPE), liquid-liquid extraction or solid-liquid extraction to produce an extract containing the at least one target compound; and optionally purifying the extract containing the at least one target compound by thermal fractionation, chromatographic separType: GrantFiled: April 7, 2011Date of Patent: March 31, 2015Assignee: Her Majesty the Queen in Right of Canada, as Represented by the Minister of EnvironmentInventors: Craig Brennan Milestone, Deborah L. MacLatchy, L. Mark Hewitt
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Patent number: 8975431Abstract: A process for preparing a 5-halophenol, ortho-substituted by an electron-donating group, is described. Also described, is a process for preparing a sulphonic ester of an ortho-substituted phenol, which is the synthesis intermediate for the ortho-substituted 5-halophenol. The process for preparing a phenol ortho-substituted by an electron-donating group and protected in the form of a sulphonic ester can include reacting a phenol ortho-substituted by an electron-donating group with a sulphonylating agent in the presence of a Lewis acid. The process for preparing a 5-halophenol ortho-substituted by an electron-donating group can include a first step of preparing a phenol ortho-substituted by an electron-donating group and protected in the form of a sulphonic ester, as described above; a second step of halogenating the protected phenol intermediate obtained in the preceding step, in the position para to the electron-donating group; and a third step of deprotecting the sulphonic ester function to hydroxyl.Type: GrantFiled: May 19, 2010Date of Patent: March 10, 2015Assignees: Rhodia Operations, Solvay (China) Co., Ltd.Inventors: Claude Mercier, Floryan De Campo, Sébastien Righini
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Publication number: 20140094628Abstract: The subject of the present invention is a method for separating phenolic compounds in salified form from a reaction medium comprising them. The method of the invention for separating phenolic compounds in salified form from an aqueous reaction medium resulting from the reaction of a phenolic compound and of glyoxylic acid in the presence of a base leading to a reaction medium comprising at least the excess of initial phenolic compound in salified form and the various mandelic compounds in salified form resulting from the reaction, is characterized by the fact that said reaction medium is brought into contact with a basic anion-exchange resin that leads to the selective attachment of the initial phenolic compound to said resin and to the recovery of an aqueous stream comprising the mandelic compounds in salified form resulting from the reaction, and that the phenolic compound in salified form attached to the resin is separated by a resin regeneration treatment.Type: ApplicationFiled: December 6, 2013Publication date: April 3, 2014Applicant: Rhodia OperationsInventor: Magali DESOUHANT-MASSACRET
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Publication number: 20130116424Abstract: A method for utilizing biomass components, namely cellulose, hemicellose, and lignin, and converting them to value-added biobased chemical products is described herein. The present method provides treatments to obtain a plurality of component streams from biomass for producing derivative products while minimizing waste products.Type: ApplicationFiled: November 9, 2011Publication date: May 9, 2013Applicant: Thesis Chemistry, LLCInventors: John R. Peterson, Christopher M. Yost, Jian Wu
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Publication number: 20130096209Abstract: The present invention provides edible compositions comprising a compound of the present invention, food products comprising such edible compositions and methods of preparing such food products. The present invention also provides methods of reducing the amount of NaCl in a food product, methods of reducing the sodium intake in a diet, and methods of reducing bitter taste in a food product.Type: ApplicationFiled: April 15, 2011Publication date: April 18, 2013Applicants: Kraft Foods Global Brands LLC, Chromocell CorporationInventors: David Hayashi, William P. Jones, Jane V. Leland, Peter H. Brown, Joseph Gunnet, Daniel Lavery, Louise Slade, Kambiz Shekdar, Jessica Langer
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Publication number: 20130072724Abstract: A process for isolating at least one target compound, such as manool, geranyl linalool, ethyl guaiacol, eugenol, veratraldehyde, squalene, terpin, cholesterol, beta-sitosterol, campesterol, stigmasterol, stigmastenol and dehydroabietic acid, from biomass, the process including steps of: obtaining a condensate from a recovery evaporator, a reverse osmosis retentate of a condensate of a pulp and paper mill, or both, the condensate, retentate or both being substantially free of higher molecular weight (approximately >1000 Da) cellulose and/or lignin and/or lignin-derived material; optionally pH adjusting and filtering the condensate to collect insoluble material; extracting the condensate, the collected insoluble material, or both, with solid phase extraction (SPE), liquid-liquid extraction or solid-liquid extraction to produce an extract containing the at least one target compound; and optionally purifying the extract containing the at least one target compound by thermal fractionation, chromatographic separType: ApplicationFiled: April 7, 2011Publication date: March 21, 2013Applicant: Her Majesty The Queen in the Right of Canada, as Represented by the Minister of EnvironmentInventors: Craig Brennan Milestone, Deborah L. MacLatchy, L. Mark Hewitt
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Publication number: 20130066097Abstract: A process for preparing a 5-halophenol, ortho-substituted by an electron-donating group, is described. Also described, is a process for preparing a sulphonic ester of an ortho-substituted phenol, which is the synthesis intermediate for the ortho-substituted 5-halophenol. The process for preparing a phenol ortho-substituted by an electron-donating group and protected in the form of a sulphonic ester can include reacting a phenol ortho-substituted by an electron-donating group with a sulphonylating agent in the presence of a Lewis acid. The process for preparing a 5-halophenol ortho-substituted by an electron-donating group can include a first step of preparing a phenol ortho-substituted by an electron-donating group and protected in the form of a sulphonic ester, as described above; a second step of halogenating the protected phenol intermediate obtained in the preceding step, in the position para to the electron-donating group; and a third step of deprotecting the sulphonic ester function to hydroxyl.Type: ApplicationFiled: May 19, 2010Publication date: March 14, 2013Applicants: RHODIA (CHINA) CO., LTD., RHODIA OPERATIONSInventors: Claude Mercier, Floryan De Campo, Sébastien Righini
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Publication number: 20120029243Abstract: The present invention relates to a composition (“composite”) comprising lignin and at least one catalyst dispersed in the composition. The invention further provides a process for producing such a catalyst- and lignin-comprising composition and its use for preparing an aromatics composition.Type: ApplicationFiled: July 28, 2011Publication date: February 2, 2012Applicant: BASF SEInventors: Emmanouil PANTOUFLAS, Roman Prochazka, Stephan Schunk
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Patent number: 8003828Abstract: The present invention provides a method of producing reduced coenzyme Q10 crystals suitable for commercial scale production thereof. According to a method of the present invention of producing a reduced coenzyme Q10 crystal which comprises a crystallization of reduced coenzyme Q10 in a solution of alcohols and/or ketones, reduced coenzyme Q10 crystal excellent in slurry properties and crystalline properties maybe obtained. Moreover, an isolation process including a crystal separation or the whole process including the isolation process maybe minimized and simplified. Thus, highly pure reduced coenzyme Q10 may be obtained in a high yield.Type: GrantFiled: July 15, 2002Date of Patent: August 23, 2011Assignee: Kaneka CorporationInventors: Takahiro Ueda, Shiro Kitamura, Yasuyoshi Ueda
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Publication number: 20110046235Abstract: The present invention relates to uses of decarboxylated phenolic acid derived from chlorogenic acid of coffee as well as products comprising decarboxylated phenolic acid derived from chlorogenic acid of coffee, especially a coffee extract, and methods of producing such products. Coffee comprises chlorogenic acids, according to the invention these chlorogenic acids can be transformed into decarboxylated phenolic acids. The resulting decarboxylated phenolic acids have antioxidant and/or anti-inflammatory properties and can be used as ingredients in food and beverage products and to treat certain health conditions.Type: ApplicationFiled: March 12, 2009Publication date: February 24, 2011Applicant: NESTEC S.A.Inventors: Rachid Bel-Rhlid, Karin Kraehenbuehl, Christophe Cavin, Thomas Wolfgang Raab, Nicolas Page
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Publication number: 20100119646Abstract: The present invention relates to the use of a selected group of phenol derivatives as components of animal feed or feed additives for the improvement of animal performance as well as to the corresponding animal feed or feed additives containing them.Type: ApplicationFiled: January 31, 2008Publication date: May 13, 2010Applicant: DSM IP ASSETS B.V.Inventors: Daniel D'Orazio, Antoine Saizieu-De, Goede Schueler, Aurelia Seon, Carlos Simoes-Nunes
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Patent number: 7230141Abstract: A process for preparing toluene derivatives of the formula I, where R1, R2 and R3 independently of one another are hydrogen, halogen, C1–C6-alkyl, hydroxyl or C1–C6-alkoxy, by hydrogenating benzaldehydes and/or benzyl alcohols of the formula II, with hydrogen in the presence of a catalyst, which is described in more detail in the description.Type: GrantFiled: January 20, 2003Date of Patent: June 12, 2007Assignee: BASF AktiengesellschaftInventors: Nils Bottke, Rolf-Hartmuth Fischer, Thomas Nöbel, Markus Rösch
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Patent number: 7208639Abstract: The present invention provides a method for obtaining reduced coenzyme Q10 which is useful as an ingredient in foods, functional nutritive foods, specific health foods, nutritional supplements, nutrients, drinks, feeds, cosmetics, medicines, remedies, preventive drugs, etc. suited for a commercial scale production in high quality and efficiently. The high-quality oily reduced coenzyme Q10 which has low viscosity and thereby easily handled may be produced by separating an aqueous phase from the reaction mixture obtainable by oily reacting oxidized coenzyme Q10 with a reducing agent in water, or by distilling off an coexisting organic solvent at or above the melting temperature of reduced coenzyme Q10 in concentrating the organic phase containing reduced coenzyme Q10. Moreover, a solution or slurry of reduced coenzyme Q10 may be obtained by adding a desired solvent to the obtained oily product, or a solid of reduced coenzyme Q10 may be produced by contacting the oily product with a seed crystal.Type: GrantFiled: July 15, 2002Date of Patent: April 24, 2007Assignee: Kaneka CorporationInventors: Takahiro Ueda, Shiro Kitamura, Yasuyoshi Ueda
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Patent number: 6512147Abstract: A mixed liquid of two or more components different in boiling temperature from each other and soluble in or compatible with each other is evaporated into a mixed vapor having a similar composition to that of the mixed liquid by using an apparatus having a thin film evaporator (1) having a feed inlet (1a) and a delivery outlet (1b), while forcedly circulating the non-evaporated portion of the mixed multi-component liquid by withdrawing the non-evaporated mixed liquid portion from the delivery side end portion of the evaporator and returning the mixed liquid portion into the feed side end portion of the evaporator through a circulating line (3), and the resultant mixed multi-component vapor can be used as a mixed material vapor for a gas phase catalytic reaction for producing, for example, a mono and/or a di-alkylether of an aromatic dihydroxy compound.Type: GrantFiled: March 28, 2002Date of Patent: January 28, 2003Assignee: UBE Industries, Ltd.Inventors: Yukio Inaba, Kazunori Fujita, Hiroshi Kofuji
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Patent number: 6013844Abstract: A process for preparing catechol monoethers or catechols of the formula Ia or Ib ##STR1## where R.sup.1 and R.sup.2 are, independently of one another, hydrogen or C.sub.1 -C.sub.8 hydrocarbon radicals, and R.sup.3 is a C.sub.1 -C.sub.8 hydrocarbon radical, which comprises a 2-hydroxycyclohexanone dialkyl ketal of the formula II or a 2-alkoxycyclohexanone of the formula III ##STR2## a) being reacted in the gas phase in the presence of palladium on zirconium oxide as catalyst to obtain compounds Ia orb) carrying out stage a) in the presence of water to obtain compounds Ib.Type: GrantFiled: July 15, 1998Date of Patent: January 11, 2000Assignee: BASF AktiengesellschaftInventors: Daniel Heineke, Uwe Dingerdissen, Joachim Wulff-Doring, Michael Hesse
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Patent number: 5319148Abstract: The preparation of pyrocatechol monoethers or pyrocatechols of the formula Ia or Ib respectively ##STR1## ( R.sup.1 and R.sup.2 =H or C.sub.1 --C.sub.8 -hydrocarbon radicals; R.sup.3 =C.sub.1 --C.sub.8 -hydrocarbon radical ) by rearranging a 2-hydroxycyclohexanone dialkyl ketal II ##STR2## a) in the gas phase in the presence of a platinmetal or in the presence of a compound of one of these metals as catalyst in order to obtain a compound Ia, orb) carrying out step a) in the presence of water in order to obtain a compound Ib. The products are used as intermediates in the synthesis of pharmaceuticals, fragrances and flavors.Type: GrantFiled: March 2, 1993Date of Patent: June 7, 1994Assignee: BASF AktiengesellschaftInventors: Michael Karcher, Horst Zimmermann, Jochem Henkelmann
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Patent number: 5248835Abstract: A monoalkylether of a dihydric phenol compound is produced at a high conversion and selectivity by catalytically dehydration reacting a dihydric phenol compound with a lower monohydric alcohol in the presence of a catalyst comprising at least one inorganic substance of the empirical formula (I):Al.sub.a P.sub.b Ti.sub.c Si.sub.d X.sub.e O.sub.f (I):wherein X is an alkali metal (Group Ia) atom, alkaline earth metal (Group IIa) atom or a metal atom of Group VIII of the Periodic Table, a, b, c, d, e and f are the numbers of Al, P, Ti, Si, X and O atoms respectively, and provided that a =1, b =1.0 to 1.9, c =0 05 to 0.5, d=0.05 to 0.2, e=0 to 0.9 and f=4.2 to 8.1, and collecting the resultant reaction product from the reaction system.Type: GrantFiled: April 16, 1992Date of Patent: September 28, 1993Assignee: Ube Industries, Ltd.Inventors: Yasushi Shiomi, Yasuo Nakamura, Takumi Manabe, Shinichi Furusaki, Masaoki Matsuda, Muneki Saito
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Patent number: 5189225Abstract: A monoalkylether of dihydric phenol compound is produced by bringing a feed gas comprising a mixture gas of a dihydric phenol compound with a monohydric alcohol compound into contact with an active catalyst component comprising at least one member selected from phosphorus compounds, and mixtures and reaction products of phosphorus compounds with boron compounds and carried on an inert solid carrier consisting of, for example, .alpha.-alumina, .gamma.-alumina, activated carbon or titania grains, and preferably having a pore volume of 0.1 ml/g or more and a specific surface area of 1 m.sup.2 /g or more, at a temperature of 200.degree. C. to 400.degree. C., and collecting the resultant reaction product from the reaction mixture.Type: GrantFiled: September 28, 1990Date of Patent: February 23, 1993Assignee: Ube Industries, Ltd.Inventors: Shinichi Furusaki, Masaoki Matsuda, Muneki Saito, Yasushi Shiomi, Yasuo Nakamura, Michio Tobita
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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: 5146010Abstract: A process for removing guaiacols from naturally-occurring cresylic acid mixtures by pyrolysis is described.Type: GrantFiled: August 9, 1991Date of Patent: September 8, 1992Assignee: Merichem CompanyInventors: James A. Brient, Marvin H. Strunk, Jr.
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Patent number: 5097078Abstract: The phenols and phenol ethers are hydroxylated by reacting such phenols/phenol ethers with hydrogen peroxide, in the presence of (a) a catalytically effective amount of an alkali metal or alkaline earth metal salt of at least one protonic acid having a pKa in water of less than -0.1, and (b) an effective amount of at least one phosphorus oxyacid.Type: GrantFiled: July 6, 1990Date of Patent: March 17, 1992Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Dominique Laucher
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Patent number: 4495353Abstract: 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: June 13, 1983Date of Patent: January 22, 1985Assignee: Sterling Drug Inc.Inventor: Robert J. Bryant
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Patent number: 4487975Abstract: Phenols, including the polyhydric phenols, are selectively monoetherified with an alkyl or alkenyl carboxylate, or admixture of compounds adapted to in situ form such carboxylate, in the presence of a salt of a carboxylic acid.Type: GrantFiled: August 11, 1982Date of Patent: December 11, 1984Assignee: Rhone-Poulenc IndustriesInventor: Serge Ratton
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Patent number: 4486611Abstract: A process for the isolation of a dihydroxybenzene-monoether from a reaction mixture containing solvent, ether and unreacted dihydroxybenzene, comprising contacting the reaction mixture with at least one hydrocarbon which is not miscible or only partially miscible with the reaction mixture, the ether selectively entering the hydrocarbon. Advantageously the reaction for the preparation of the monoether is carried out in an alcohol, a ketone, a dipolar aprotic solvent or a polyhydroxyalkyl ether, or a mixture thereof with water, the hydrocarbon used as extracting agent has a boiling point between about 80.degree. and 300.degree. C., and the extraction is carried out in the presence of water whereby there is an increase in the selectivity of the extraction.Type: GrantFiled: August 30, 1982Date of Patent: December 4, 1984Assignee: Bayer AktiengesellschaftInventors: Manfred Lenthe, Udo Allenbach, Gerhard Buttner, Karl-Friedrich Christmann
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Patent number: 4473713Abstract: At least one of the other functions comprising an aryl-aliphatic ether, e.g., veratrol, is catalytically hydrolyzed with water, e.g., to guaiacol, in the presence of a catalytically effective amount of a salt of a carboxylic acid.Type: GrantFiled: September 27, 1982Date of Patent: September 25, 1984Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Serge Ratton
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Patent number: 4396783Abstract: A process for the hydroxylation of aromatic hydrocarbons by hydrogen peroxide, consisting in reacting said compounds in the presence of synthetic zeolites which contain heteroatoms, both replaced and exchanged.The reaction is carried out at a temperature comprised between 80.degree. C. and 120.degree. C. and in the presence of the hydrocarbon only or in the presence of a solvent which permits, at least partially, to admix the aromatic hydrocarbon with the hydrogen peroxide.Type: GrantFiled: September 4, 1981Date of Patent: August 2, 1983Assignee: Anic S.p.A.Inventors: Antonio Esposito, Marco Taramasso, Carlo Neri
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Patent number: 4254288Abstract: A method of producing an aromatic compound comprises dehydrogenating a compound having a six-membered carbocyclic ring in the molecule, the ring having a degree of saturation greater than that of a benzene ring, the dehydrogenation being carried out in the presence of a catalyst system comprising elemental palladium together with sodium carbonate and sulphur. The compound to be dehydrogenated may be a substituted cyclohexane. When the substituted cyclohexane is an alkoxycyclohexanol, the aromatic compound produced is an alkoxy phenol. In particularly useful aspect of the invention the substituted cyclohexane is a 2-alkoxycyclohexanol, the aromatic compound produced being an ortho-alkoxy phenol.Type: GrantFiled: July 6, 1979Date of Patent: March 3, 1981Assignee: Coalite Group LimitedInventor: Keith Gladwin
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Patent number: 4220605Abstract: A process for the production of alcohols and/or aldehydes which comprises subjecting a toluene derivative having an ether linkage or linkages of the general formula: ##STR1## wherein RO is an ether grouping where R stands for a hydrocarbyl group with 1.about.20 carbon atoms which may carry an inert substituent or substituents and n stands for an integer of 1.about.2, to auto-oxidation with molecular oxygen in liquid phase to form the corresponding alcohol and/or aldehyde, characterized in that the reaction is carried out by using a lower saturated fatty acid and/or an anhydride thereof as solvent in the presence of a soluble cobalt salt and a bromine ion-supplying substance at a reaction temperature ranging from 30.degree. C. to 200.degree. C. in such manner that the conversion rate of the toluene derivative does not exceed 90%.Type: GrantFiled: December 23, 1977Date of Patent: September 2, 1980Assignees: Director General of Agency of Industrial Science and Technology, Sanko Chemical Co. Ltd., Nippon Soda Co. Ltd.Inventor: Juichi Imamura
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Patent number: 4208350Abstract: Phenol, ortho-cresol, meta- and para-cresols, guaiacol, vanillin, acetovanillone and other phenols are separated from alkaline pulping spent liquors by extracting the alkaline liquors with a lower aliphatic alcohol having from 2-5 carbon atoms inclusive, separating the solvent and aqueous phases, and thereafter separating the phenols from the solvent phase.Type: GrantFiled: March 6, 1978Date of Patent: June 17, 1980Assignee: Boise Cascade CorporationInventors: William M. Hearon, Cheng F. Lo
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Patent number: 4166914Abstract: O-alkoxyphenols are produced from cyclohexanone or cyclohexanol by chlorination of cyclohexanone or cyclohexanol to trichlorocyclohexanone and reaction of the trichlorocyclohexanone with an aliphatic, monohydric alcohol having one to four carbon atoms and a base to form an intermediate compound or compounds which are further reacted to convert the intermediate compound or compounds to an o-alkoxyphenol.Type: GrantFiled: May 31, 1977Date of Patent: September 4, 1979Assignee: Carl E. Van WinckelInventors: Carl E. Van Winckel, David H. Dolphin, Elena Dumitrescu, Kent F. Van Winckel
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Patent number: 4129601Abstract: New and valuable pyrocatechol derivatives and a process for their preparation. The pyrocatechol derivatives have the formula ##STR1## wherein: R denotes alkyl of from 1 to 4 carbon atoms which may be substituted with halogen; alkenyl having up to 4 carbon atoms which may be substituted with halogen; alkynyl having up to 5 carbon atoms which may be substituted with halogen; or benzyl;R.sup.1 denotes hydrogen or alkyl of from 1 to 4 carbon atoms;R.sup.2 denotes benzyl or alkyl of from 1 to 3 carbon atoms which may be substituted with halogen, methoxy or ethoxy;R.sup.3 denotes alkyl of from 1 to 4 carbon atoms; cycloalkyl of from 3 to 7 carbon atoms; .beta.-chlorethyl; methoxyethyl; ethoxyethyl; alkenyl of from 2 to 4 carbon atoms; alkynyl of from 2 to 4 carbon atoms; acetyl; propionyl;R.sup.1 and R.sup.2 when taken together with the carbon atom to which they are attached form a cyclopentyl or cyclohexyl ring; andR.sup.1 and R.sup.Type: GrantFiled: August 2, 1976Date of Patent: December 12, 1978Assignee: BASF AktiengesellschaftInventors: Karl Kiehs, Rolf Huber