By Isomerization Patents (Class 568/906)
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Patent number: 8603201Abstract: The present invention is to provide a novel method for manufacturing various organic compounds from two or more kinds of alcohol, or one kind of alcohol having three or more carbon atoms. It is a method for synthesizing one kind of, or two or more kinds of organic compounds comprising allowing two or more kinds of alcohol or one kind of alcohol having three or more carbon atoms to contact a calcium phosphate catalyst such as hydroxyapatite, or hydrotalcite.Type: GrantFiled: February 23, 2009Date of Patent: December 10, 2013Assignee: Kabushiki Kaisha SangiInventors: Takashi Tsuchida, Shuji Sakuma, Tetsuya Yoshioka, Jun Kubo
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Patent number: 8563785Abstract: A process for isomerizing olefinically unsaturated alcohols over supported noble metal catalysts with a support based on carbon in an oxygenous atmosphere.Type: GrantFiled: September 10, 2012Date of Patent: October 22, 2013Assignee: BASF SEInventors: Michael Limbach, Joaquim Henrique Teles, Radwan Abdallah, Torsten Mäurer, Thorsten Johann, Manuel Danz
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Patent number: 8536341Abstract: The invention relates to a process of reacting a primary allylic alcohol with a compound containing a) a metal selected from the group consisting of Ag, Au, Ce, Mn, Ni, Ru, Re, Zn and Co preferably Ag and b) an oxidant like TEMPO (2,2?,6,6?-tetra-methylpiperidin-1-oxyl) or its derivates and c) a co-oxidants selected from the group of peroxodisulfates (PDS), H2SO5, H2O2, NaOCl, O2, KOCl, and air.Type: GrantFiled: February 15, 2008Date of Patent: September 17, 2013Assignee: DSM IP Assets B.V.Inventors: Werner Bonrath, Jean-Francois Eckhard, Manfred L. Eggersdorfer, Ramona Hinze, Wolfgang F. Hölderich, Michael H. Valkenberg
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Patent number: 8263813Abstract: A process for isomerizing olefinically unsaturated alcohols over supported noble metal catalysts with a support based on carbon in an oxygenous atmosphere.Type: GrantFiled: February 27, 2009Date of Patent: September 11, 2012Assignee: BASF SEInventors: Michael Limbach, Joaquim Henrique Teles, Radwan Abdallah, Torsten Mäurer, Thorsten Johann, Manuel Danz
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Publication number: 20110015412Abstract: The invention relates to a process of reacting a primary allylic alcohol with a compound containing a) a metal selected from the group consisting of Ag, Au, Ce, Mn, Ni, Ru, Re, Zn and Co preferably Ag and b) an oxidant like TEMPO (2,2?,6,6?-tetra-methylpiperidin-1-oxyl) or its derivates and c) a co-oxidants selected from the group of peroxodisulfates (PDS), H2505, H2O2, NaOCl, O2, KOCl, and air.Type: ApplicationFiled: February 15, 2008Publication date: January 20, 2011Applicant: DSM IP ASSETS B.V.Inventors: Werner Bonrath, Jean-Francois Eckhardt, Manfred L. Eggersdorfer, Ramona Hinze, Wolfgang F. Hölderich, Michael H. Valkenberg
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Patent number: 7132576Abstract: The present invention relates to a process for isomerizing reactant allyl alcohols of the formula (I) to product allyl alcohols of the general formula (II) where R1 to R5 are each hydrogen or a mono- or polyunsaturated or saturated C1–C12-alkyl radical, which can be substituted or unsubstituted, in both directions of the equilibrium, which comprises isomerizing in the presence of a dioxotungsten(VI) complex of the general formula (III), where L1, L2 are each independently a ligand selected from the group consisting of the aminoalcohols, the aminophenols and mixtures thereof, m, n are each 1 or 2, new dioxotungsten(VI) complexes, and also their use.Type: GrantFiled: December 4, 2002Date of Patent: November 7, 2006Assignee: BASF AktiengesellschaftInventors: Frank Haese, Klaus Ebel
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Patent number: 7126033Abstract: The present invention relates to a process for isomerizing reactant allyl alcohols to product allyl alcohols in the presence of a catalyst, wherein the reactant allyl alcohol is rearranged to product allyl alcohol in semicontinuous or continuous mode in a catalyst-containing suitable reactor. In particular, the process according to the invention is used to prepare linalool from Geraniol and/or nerol.Type: GrantFiled: December 4, 2002Date of Patent: October 24, 2006Assignee: BASF AktiengesellschaftInventors: Frank Haese, Klaus Ebel, Kirsten Burkart, Signe Unverricht, Peter Münster
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Patent number: 6989468Abstract: The present invention relates to a process for the isomerization of precursor allyl alcohols of the formula (I) to product allyl alcohols of the formula (II) where R1 to R5 are hydrogen or a mono- or polyunsaturated or saturated C1-C12-alkyl radical, which may be substituted, in both directions of the equilibrium, wherein the reaction takes place in the presence of an oxoperoxotungsten(VI) complex of the formula (III), where L1, L2 in each case independently of one another are water or a free coordination site, or are optionally a ligand chosen from the group of aminoalcohols, aminophenols, aminocarboxylic acids or mixtures thereof or mixtures of amines with alcohols, phenols or carboxylic acids, m is the number 1 or 2 n is a number from 1 to 6 p is a number from 1 to 6, where in the case of p>1 a di- or polynuclear complex is formed, and also to novel oxoperoxotungsten(VI) complexes and to the use thereof.Type: GrantFiled: September 18, 2001Date of Patent: January 24, 2006Assignee: BASF AktiengesellschaftInventors: Frank Haese, Klaus Ebel
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Publication number: 20040097765Abstract: The present invention relates to a process for the isomerization of precursor allyl alcohols of the formula (I) to product allyl alcohols of the formula (II) 1Type: ApplicationFiled: March 11, 2003Publication date: May 20, 2004Inventors: Frank Haese, Klaus Ebel
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Publication number: 20020128525Abstract: Provided is citronellol, which has an elegant rosy fragrance and is extremely useful for fragrance impartation to aromatic articles A mixture of an alkylamine and isoprene in a molar ratio of from 1:4 to 1:4.5 is subjected to telomerization at 80 to 100° C. for 2.5 to 3.5 hours in the presence of an alkyllithium catalyst and/or phenyllithium catalyst to obtain a nerylamine compound containing 2 to 10 wt % &agr;-nerylamine compound represented by general formula (4).Type: ApplicationFiled: March 18, 2002Publication date: September 12, 2002Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Shinya Yamada, Yoshiki Okeda, Yoji Hori, Toshimitsu Hagiwara
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Publication number: 20020004620Abstract: Provided is citronellol, which has an elegant rosy fragrance and is extremely useful for fragrance impartation to aromatic articles. A mixture of an alkylamine and isoprene in a molar ratio of from 1:4 to 1:4.5 is subjected to telomerization at 80 to 100° C. for 2.5 to 3.5 hours in the presence of an alkyllithium catalyst and/or phenyllithium catalyst to obtain a nerylamine compound containing 2 to 10 wt % &agr;-nerylamine compound represented by general formula (4).Type: ApplicationFiled: April 6, 2001Publication date: January 10, 2002Inventors: Shinya Yamada, Yoshiki Okeda, Yoji Hori, Toshimitsu Hagiwara
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Patent number: 6278031Abstract: The fixed-bed catalyst comprises palladium and selenium or tellurium or a mixture of selenium and tellurium on a silicon dioxide support and has a BET surface area of from 80 to 380 m2/g and a pore volume of from 0.6 to 0.95 cm3/g in the pore diameter range from 3 nm to 300 &mgr;m, with from 80 to 95% of the pore volume being in the pore diameter range from 10 to 100 nm. It is prepared by impregnating a silicon dioxide support with a solution of a palladium compound and a selenium compound or tellurium compound or a mixture of a selenium compound and a tellurium compound, drying it and reducing it in the presence of hydrogen. The catalyst is used, in particular, for isomerizing 3-buten-1-ol compounds.Type: GrantFiled: January 16, 2001Date of Patent: August 21, 2001Assignee: BASF AktiengesellschaftInventors: Franz Josef Bröcker, Werner Aquila, Klemens Flick, Gerd Kaibel, Ernst Langguth
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Patent number: 6211114Abstract: The fixed-bed catalyst comprises palladium and selenium or tellurium or a mixture of selenium and tellurium on a silicon dioxide support and has a BET surface area of from 80 to 380 m2/g and a pore volume of from 0.6 to 0.95 cm3/g in the pore diameter range from 3 nm to 300 &mgr;m, with from 80 to 95% of the pore volume being in the pore diameter range from 10 to 100 nm. It is prepared by impregnating a silicon dioxide support with a solution of a palladium compound and a selenium compound or tellurium compound or a mixture of a selenium compound and a tellurium compound, drying it and reducing it in the presence of hydrogen. The catalyst is used, in particular, for isomerizing 3-buten-1-ol compounds.Type: GrantFiled: November 6, 1997Date of Patent: April 3, 2001Assignee: BASF AktiengesellschaftInventors: Franz Josef Bröcker, Werner Aquila, Klemens Flick, Gerd Kaibel, Ernst Langguth
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Patent number: 6180839Abstract: A process is described for the continuous preparation of dimethylvinylcarbinol (DMVC) by continuously reacting prenol with the aqueous solution of a protic acid in the still or in the lower part of a rectification column while distilling off the DMVC formed in the form of an azeotropic mixture with water, which comprises a) during the reaction ensuring that as far as possible no liquid two-phase mixture forms in the reaction mixture, b) distilling off the DMVC which forms at a reflux ratio of at least 2, as a result of which there is virtually no more prenol present in the distillate from the column, and c) setting the reaction volume and/or the amount of prenol added per hour and/or the concentration of protons in the reaction mixture in such a manner that the quotient, defined as residence time concentration coefficient, of the reaction volume and the volume of prenol added per hour multiplied by the concentration of protons in the reaction mixture has a value between 0.Type: GrantFiled: March 10, 1999Date of Patent: January 30, 2001Assignee: BASF AktiengesellschaftInventors: Matthias Kiefer, Wolfgang Siegel, Jörg Therre, Melanie Pahl, Werner Aquila, Ulrich Sch{umlaut over (a)}fer-L{umlaut over (u)}derssen
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Patent number: 5998680Abstract: Allyl alcohols are isomerized in aqueous solution in the presence of protonic acids, with the pH of the reaction mixture being adjusted to the range from 2 to 5 with an acid concentration below 0.16 mol per liter of the reaction mixture or with a buffer which comprises the protonic acid.Type: GrantFiled: February 24, 1998Date of Patent: December 7, 1999Assignee: BASF AktiengesellschaftInventors: Matthias Kiefer, Wolfgang Siegel, Jorg Therre, Melanie Pahl, Werner Aquila, Ulrich Schafer-Luderssen, Udo Rheude
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Patent number: 5973211Abstract: A method of isomerizing lutein to yield a mixture of epimers of zeaxanthin includes the following steps: mixing a lutein-containing extract in a glycol solution to obtain a mixture, treating the mixture with alkali to obtain an alkali-containing mixture, reacting the alkali-containing mixture in the presence of heat for a duration consistent with achieving a desired level of isomerization of lutein to zeaxanthin.Type: GrantFiled: July 18, 1997Date of Patent: October 26, 1999Assignee: Prodemex, S.A. DE C.V.Inventor: Gustavo Rodriguez
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Patent number: 5349097Abstract: A process for the catalytic isomerization of secondary .alpha.-alkenols of formula I ##STR1## in which R.sup.1 is a C.sub.1 -C.sub.20 alkyl group or a C.sub.2 -C.sub.2 alkenyl group and in which R.sup.2 stands for hydrogen, a halogen atom, a C.sub.1 -C.sub.10 alkoxy group, a carbonyl group, or a C.sub.1 -C.sub.20 alkyl group and in which R.sup.1 and R.sup.2 can be joined together to complete a five-membered or six-membered carbocyclic ring, to primary .alpha.-alkenols of formula II ##STR2## or for the isomerization of primary .alpha.-alkenols of formula II to secondary .alpha.-alkenols of formula I, wherein the isomerization is carried out in the presence of organotrioxorhenium(VII) compounds of formula III ##STR3## in which R.sup.3 is a C.sub.1 -C.sub.10 alkyl group, a cyclopentadienyl group substituted by from one to five C.sub.1 -C.sub.4 alkyl groups, an unsubstituted cyclopentadienyl group, a C.sub.6 -C.sub.10 aryl group, or a C.sub.7 -C.sub.Type: GrantFiled: July 29, 1993Date of Patent: September 20, 1994Assignee: BASF AktiengesellschaftInventors: Alfred Thome, Michael Roeper, Heinz-Josef Kneuper
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Patent number: 5110961Abstract: The invention relates to a catalytic process for the synthesis of an alcohol by reaction of an epoxide with a nucleophilic compound containing a labile hydrogen, such as an alcohol, a phenol, a primary amine or a carboxylic acid.The catalyst is a metal complex of general formula (I)[M[Co(CO).sub.4 ].sub.2 ].sub.x in which x is equal to 1 or 2 and M denotes tin, lead and cadmium.The reaction preferably takes place in the presence of carbon monoxide.This process makes it possible to increase the yield and the selectivity of the reaction and the stereoselectivity for alcohol in the case of which the hydroxyl formed is attached to the least hindered carbon atom of the epoxide.The invention also relates to the new complexes of formula (I) in which x equals 2.It also relates to a process for the electrosynthesis of these new compounds by electroreduction of Co.sub.2 (CO).sub.Type: GrantFiled: December 14, 1990Date of Patent: May 5, 1992Assignee: Societe Nationale des Poudres et ExplosifsInventors: Serge Lecolier, Andre Mortreux, Francis Petit, Henri Samain
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Patent number: 4720558Abstract: Process for inverting the configuration of secondary alcohols in which the hydroxyl group is attached to an asymmetric carbon atom, in accordance with which the secondary alcohols are esterified, with inversion of their configuration, by conversion into isourea ethers and reaction of these isourea ethers with carboxylic acids, and the esters are then saponified with retention of the configuration of the secondary alcohols.Type: GrantFiled: March 11, 1986Date of Patent: January 19, 1988Assignee: Bayer AktiengesellschaftInventor: Johannes Kaulen
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Patent number: 4510331Abstract: There are disclosed a process for producing 7-octen-1-al which comprises isomerizing 2,7-octadien-1-ol in the presence of a catalyst comprising oxides of at least two metals selected from the group consisting of copper, chromium and zinc and processes for producing derivatives of 7-octen-1-al.Type: GrantFiled: June 22, 1982Date of Patent: April 9, 1985Assignee: Kuraray Company, Ltd.Inventors: Noriaki Yoshimura, Masuhiko Tamura
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Patent number: 4460801Abstract: New unsaturated fatty alcohols of the formula: ##STR1## in which n=2 or 4 are provided and are prepared by the novel process of reacting butadiene with water in the presence of a palladium salt and orthoboric acid, B(OH).sub.3, in a polar aprotic solvent.Type: GrantFiled: June 28, 1983Date of Patent: July 17, 1984Assignee: Rhone-Poulenc IndustriesInventor: Didier Morel
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Patent number: 4338170Abstract: A cis-trans isomerization of a cis-.beta.-.gamma.-unsaturated alcohol or its ester having the formula ##STR1## wherein R.sub.1 represents hydrogen atom or a C.sub.1 -C.sub.5 alkyl group; X represents hydrogen atom or ##STR2## and R.sub.2 represents a hydrocarbon moiety or a hydroxyhydrocarbon moiety; R.sub.3 represents hydrogen atom or a hydrocarbon moiety into a transform, in the presence of a mercaptan as a catalyst, is provided. It can be also attained in the presence of a mercaptan and/or a disulfide as a catalyst in an inert gas environment with an initiator. It can be also attained in the presence of a mercaptan under an irradiation, if desired with a small amount of an initiator.Type: GrantFiled: May 23, 1980Date of Patent: July 6, 1982Assignee: Nissan Chemical Industries, Ltd.Inventors: Atsuo Murata, Syuji Tsuchiya, Hideo Suzuki
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Patent number: 4337372Abstract: The invention provides a novel method for the cis to trans isomerization of an alkenyl alcohol in a very simple process. The inventive method comprises heating the cis-isomer at a temperature of, for example, 150.degree. to 200.degree. C. in the presence of selenium metal in a powdery form with agitation.Type: GrantFiled: May 22, 1981Date of Patent: June 29, 1982Assignee: Shin-Etsu Chemical Company LimitedInventors: Toshinobu Ishihara, Akira Yamamoto, Kenichi Taguchi
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Patent number: 4310709Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.Type: GrantFiled: April 23, 1980Date of Patent: January 12, 1982Assignee: BASF AktiengesellschaftInventor: Walter Rebafka
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Patent number: 4219683Abstract: Olefinically unsaturated compounds, such as nitriles, alcohols, esters, ethers and the like are isomerized to other unsaturated compounds in the presence of a palladium-thorium oxide catalyst and hydrogen.Type: GrantFiled: September 25, 1978Date of Patent: August 26, 1980Assignee: Phillips Petroleum CompanyInventor: Yulin Wu
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Patent number: 4087472Abstract: An olefinic hydrocarbon is isomerized utilizing a catalyst system consisting essentially of a mixture of a nickel complex of the formula (R.sub.3 P).sub.2 NiX.sub.2 and an alkali metal borohydride.Type: GrantFiled: August 16, 1976Date of Patent: May 2, 1978Assignee: Phillips Petroleum CompanyInventor: William B. Hughes