Polyalkylol Substituted Alkane (e.g., Pentaerythritol, Trimethylolethane, Ect.) Patents (Class 568/853)
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Patent number: 7321070Abstract: The present invention is directed to asymmetric chiral labeled glycerols including at least one chiral atom, from one to two 13C atoms and from zero to four deuterium atoms bonded directly to a carbon atom, e.g., (2S) [1,2-13C2]glycerol and (2R) [1,2-13C2]glycerol, and to the use of such chiral glycerols in the preparation of labeled amino acids.Type: GrantFiled: July 30, 2003Date of Patent: January 22, 2008Assignee: Los Alamos National Security, LLCInventors: Rodolfo A. Martinez, Clifford J. Unkefer, Marc A. Alvarez
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Patent number: 7307194Abstract: The present invention provides a process for preparing 1,6-hexanediol from a carboxylic acid mixture which comprises adipic acid, 6-hydroxycaproic acid and small amounts of 1,4-cyclohexanediols and is obtained as a by-product in the oxidation of cyclohexane to cyclohexanone/cyclohexanol with oxygen or oxygen-containing gases and by water extraction of the reaction mixture, by esterification of the acids and hydrogenation, in which a) the mono- and dicarboxylic acids present in the aqueous dicarboxylic acid mixture are reacted with a low molecular weight alcohol to give the corresponding carboxylic esters, b) the resulting esterification mixture is freed of excess alcohol and low boilers in a first distillation stage, c) a separation of the bottom product is carried out in a second distillation stage into an ester fraction substantially free of 1,4-cyclohexanediols and a fraction comprising at least the majority of the 1,4-cyclohexanediols, d) the ester fraction substantially free of 1,4-cyclohexanediols isType: GrantFiled: October 27, 2005Date of Patent: December 11, 2007Assignee: BASF AktiengesellschaftInventors: Tilman Sirch, Gerd-Dieter Tebben, Ludwig E. Heck, Armin Diefenbacher, Alfred Krause, Franz Borgel
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Patent number: 7301058Abstract: The invention relates to a method for increasing yield in the production of polyvalent alcohols, especially trimethylolpropane, obtained by condensing formaldehyde with a higher aldehyde. According to the inventive method, acid treatment is carried out on a mixture (high-boiling fraction) that is obtained by reprocessing, contains derivatives of said alcohols and has a higher boiling point than the respective alcohol, and the polyvalent alcohol is recovered from the acid-treated high-boiling fraction. The inventive method is characterised in that the water content of the high-boiling fraction amounts to between 20 and 90 wt. % in relation to the entire mixture of the high-boiling fraction and water.Type: GrantFiled: July 18, 2003Date of Patent: November 27, 2007Assignee: BASF AktiengesellschaftInventors: Alexander Wartini, Tilman Sirch, Johann-Peter Melder, Matthias Dernbach
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Patent number: 7253326Abstract: The present invention relates to a method for preparing trimethylolpropane (TMP) comprising the steps of: 1) synthesizing trimethylolpropane by using n-butyl aldehyde, an aqueous solution of formaldehyde and an aqueous solution of alkali metal hydroxide through aldol condensation reaction and Cannizzaro reaction; 2) extracting trimethylolpropane from a resultant mixture of the step 1) by contacting the resultant mixture with an alcohol having 6 to 10 carbons; 3) removing alkali metal ion from a resultant extract of the step 2) by contacting the resultant extract with water; and 4) distilling the alkali metal ion-removed extract obtained from the step 3).Type: GrantFiled: April 10, 2006Date of Patent: August 7, 2007Assignee: LG Chem, Ltd.Inventors: Sung Shik Eom, Dong Hyun Ko, Ji Joong Moon, Jae Hoon Choe, Dae Sun Rew
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Patent number: 7211701Abstract: The present invention relates to a process for preparing trimethylolpropane having a low APHA color number.Type: GrantFiled: December 18, 2002Date of Patent: May 1, 2007Assignee: Lanxess Deutschland GmbHInventors: Dirk Müller, Paul Wagner, Brian Schwegler, Ulrich Notheis, Ralph Armbrust, Hans-Detlef Heinz, Alexander Wagner
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Patent number: 7157607Abstract: A process of manufacture of polytrimethylene ether glycol comprising: (a) polycondensing reactant comprising diol selected from the group consisting of 1,3-propanediol, 1,3-propanediol dimer and 1,3-propanediol trimer or mixtures thereof in the presence of acid polycondensation catalyst to form polytrimethylene ether glycol; (b) adding water to the polytrimethylene ether glycol to form an aqueous mixture; (c) heating the aqueous mixture to hydrolyze acid esters formed during the acid catalyzed polycondensation; (d) adding to the hydrolyzed aqueous mixture organic solvent that is miscible with polytrimethylene ether glycol to form (i) organic phase containing the polytrimethylene ether glycol and residual acid polycondensation catalyst from the polycondensing and (ii) aqueous phase; (e) separating the aqueous phase and the organic phase; (f) adding base to the separated organic phase to neutralize the residual acid polycondensation catalyst by forming salts of the residual acid polycondensation catalyst; (gType: GrantFiled: August 16, 2005Date of Patent: January 2, 2007Assignee: E. I. du Pont de Nemours and CompanyInventors: Hari Babu Sunkara, Howard C. Ng, Wei Zheng
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Patent number: 7087800Abstract: A process for producing a polyol by reacting an aliphatic aldehyde with formaldehyde in the presence of a basic catalyst, which comprises a step of concentration which comprises removing water and unreacted formaldehyde from a reaction liquid by distillation; a step of extraction which comprises extracting the polyol from a concentrated reaction liquid with an extracting reagent; a step of washing with water which comprises washing an extract liquid with water and separating the liquid into an oil layer containing the polyol and an aqueous layer; wherein by useing an specific aliphatic aldehyde as the extracting agent and recovering the extracting reagent from the oil layer containing the polyol after adjusting pH of the oil layer, a high purity polyhydric alcohol can be obtained at a high yield with suppressed formation of byproducts such as acetal compounds and aldol compounds.Type: GrantFiled: June 6, 2001Date of Patent: August 8, 2006Assignee: Mitsubishi Gas Chemical Company, INCInventors: Teruyuki Ninomiya, Toshio Watanabe, Atsushi Iwamoto, Soemu Miyashita, Masafumi Watanabe
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Patent number: 7057080Abstract: A process is provided for improving the color number of polyhydric alcohols, especially trimethylolpropane, by catalytic hydrogenation, the polyhydric alcohol used in the hydrogenation having been purified by distillation following its preparation, wherein the hydrogenation is carried out in the presence of a macroporous supported heterogeneous catalyst containing, as the active metal, at least one metal of subgroups VII to X of the Periodic Table.Type: GrantFiled: October 11, 2001Date of Patent: June 6, 2006Assignee: BASF AktiengesellschaftInventors: Matthias Dernbach, Christoph Sigwart, Michael Hesse, Steffen Maas
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Patent number: 6949684Abstract: An object of the present invention is to provide a process wherein 1,2,4-butanetriol can be obtained safely, easily and inexpensively without causing problems concerning wastewater. A malic diester, 3-hydroxy-?-butyrolactone or 3,4-dihydroxybutanoate represented by the following formulae (I), or a mixture thereof is reduced with sodium borohydride in an organic solvent to give 1,2,4-butanetriol represented by the following formula (II). When an optically active substance is used as the above-mentioned starting compound, substantially no recemization occurs during the reduction, and optically active 1,2,4-butanetriol is obtained.Type: GrantFiled: July 8, 2002Date of Patent: September 27, 2005Assignee: Daiso Co., Ltd.Inventors: Kousei Ikai, Masafumi Mikami, Yoshiro Furukawa, Takeshi Urano, Seiji Ohtaka
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Patent number: 6809224Abstract: Formaldehyde is removed by distillation from reaction solutions containing a methlolated alkanal which was obtained from the reaction of formaldehyde with an alkanal which has at least one acidic hydrogen atom &agr; to the carbonyl function or from the reaction of a 2-alkylacrolein or acrolein with water and formaldehyde, by a process in which this reaction was carried out in the presence of catalytic amounts of organic amine. The process permits the improved removal of formaldehyde from the reaction mixture and furthermore facilitates the hydrogenation of the alkanals thus obtained to give polyols.Type: GrantFiled: June 26, 2002Date of Patent: October 26, 2004Assignee: BASF AktiengesellschaftInventors: Matthias Dernbach, Detlef Kratz, Achim Stammer, Gerhard Schulz
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Patent number: 6787677Abstract: In a process for the catalytic hydrogenation of a carbonyl compound or a mixture of two or more carbonyl compounds in the presence of catalyst tablets which comprise an inorganic, TiO2-containing support and, as active component, copper or a mixture of copper with at least one metal selected from the group consisting of zinc, aluminum, cerium, nobel metals and metals of transition group VIII and whose copper surface area is not more than 10 m2/g, the diameter d and/or the height h of the tablets is less than 3 mm.Type: GrantFiled: September 29, 2003Date of Patent: September 7, 2004Assignee: BASF AktiengesellschaftInventors: Michael Koch, Steffen Maas, Wolfgang Jürgen Pöpel, Matthias Dernbach
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Patent number: 6727395Abstract: A process for preparing 1,6-hexanediol from a carboxylic acid mixture comprising adipic acid, 6-hydroxycaproic acid and small amounts of 1,4-cyclohexanediols which is obtained as by-product in the oxidation of cyclohexane to cyclohexanone/cyclohexanol after water extraction of the reaction mixture followed by extraction with aqueous sodium hydroxide solution, by esterification of the acids and hydrogenation comprises a) liberating the carboxylic acids from the alkaline extract by addition of a mineral acid, b) fractionating the organic phase comprising carboxylic acids to give a distillate comprising the low molecular weight monocarboxylic acids and a residue comprising adipic acid and 6-hydroxycaproic acid, c) reacting the monocarboxylic an dicarboxylic acids present in the aqueous dicarboxylic acid mixture with a low molecular weight alcohol to give the corresponding carboxylic esters, d) freeing the esterification mixture obtained of excess alcohol and low boilers in a first distillation step, e) fracType: GrantFiled: December 19, 2001Date of Patent: April 27, 2004Assignee: BASF AktiengesellschaftInventors: Frank Stein, Thomas Krug, Thomas Nöbel, Harald Rust
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Patent number: 6692616Abstract: A process is disclosed for the purification, by distillation, of trimethylolpropane originating from the hydrogenation of 2,2-dimethylolbutanal, said process including the following steps: (a) reaction of n-butyraldehyde with formaldehyde in the presence of catalytic amounts of a tertiary amine, and hydrogenation of the resulting mixture to give a mixture containing trimethylolpropane; (b) separation of water, methanol, trialkylamine and/or trialkylammonium formate by distillation; (c) heating of the residue obtained in (b) under reduced pressure to a temperature at which TMP is volatile and compounds boiling above TMP are cleaved, in order to separate off, by distillation, TMP and compounds more volatile than TMP; (d) distillation of the distillate obtained in (c) in order to separate off the more volatile compounds and recover pure TMP; and (e) optional distillation of the TMP obtained in (d) in order to recover TMP with a low APHA color index.Type: GrantFiled: June 26, 2002Date of Patent: February 17, 2004Assignee: BASF AktiengesellschaftInventors: Matthias Dernbach, Detlef Kratz, Achim Stammer, Harald Rust, Gerhard Schulz
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Patent number: 6646170Abstract: The present invention relates to novel ether compounds, compositions comprising ether compounds, and methods useful for treating and preventing cardiovascular diseases, dyslipidemias, dysproteinemias, and glucose metabolism disorders comprising administering a composition comprising an ether compound. The compounds, compositions, and methods of the invention are also useful for treating and preventing Alzheimer's Disease, Syndrome X, peroxisome proliferator activated receptor-related disorders, septicemia, thrombotic disorders, obesity, pancreatitis, hypertension, renal disease, cancer, inflammation, and impotence. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.Type: GrantFiled: April 26, 2002Date of Patent: November 11, 2003Assignee: Esperion Therapeutics, Inc.Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
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Patent number: 6593502Abstract: The invention relates to a process for the preparation of polyols having 3 or 4 hydroxyl groups, from an aldehyde and formaldehyde in the presence of water, followed by hydrogenation of the aldolisation product in the presence of a hydrogenation catalyst at an elevated temperature. The aledhyde is obtained by an aldolisation reaction of an aldehyde having at least two &agr;-hydrogen atoms and a formula according to R1CH2CHO, wherein R1 is selected from a group comprising hydrogen, alkyl groups having 1-7 carbon atoms which can have cycloalkyl substituents, cycloalkyl groups, aryl groups and aralkyl groups with 1-7 carbon atoms is the alkyl chain, with formaldehyde in the presence of water in an amount of 20-70 wt %, preferably 40-60 wt % and in the presence of an anion exchange resin. The hydrogenation is preferably carried out in the presence of water.Type: GrantFiled: January 2, 2002Date of Patent: July 15, 2003Assignee: Dynea Chemicals OyInventors: Tapio Salmi, Valentina Serra-Holm, Tiina-Kaisa Rantakylä, Päivi Mäki-Arvela, Lars-Peter Lindfors, Hannu Nousiainen
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Patent number: 6586641Abstract: A process is provided for increasing the yield in the preparation of polyhydric alcohols obtained from methylolated alkanals by hydrogenation, wherein derivatives of these alcohols are decomposed by adding 5 ppm to 1% by weight, preferably 100 to 1000 ppm, of a suitable acid to an anhydrous mixture containing these derivatives, heating the mixture to temperatures of 100 to 300° C. and then separating off the polyhydric alcohol by distillation. This process makes it possible simply and efficiently to decompose compounds which boil above the polyhydric alcohol and are unwanted by-products of its synthesis.Type: GrantFiled: June 26, 2002Date of Patent: July 1, 2003Assignee: BASF AktiengesellschaftInventors: Matthias Dernbach, Detlef Kratz, Achim Stammer, Gerhard Schulz
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Patent number: 6538163Abstract: A method for reducing a malonate having the formula R1R2C(CO2R3)(CO2R4) to a diol having the formula R1R2C(CH2OH)2 comprising treating said malonate with sodium aluminum hydride.Type: GrantFiled: April 25, 2002Date of Patent: March 25, 2003Assignee: Rohm and Haas CompanyInventors: Won Suh Park, John Hiroshi Yamamoto
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Patent number: 6506947Abstract: The subject-matter of the invention is a fluorinated diol and its process of preparation. The fluorinated diol corresponds to the formula (I): CnF2n+1—A—CH2OCH2—C(CH2OH)2—R in which n has a value from 2 to 20 and A means —CH═CH— or —CH2CH2— and R is an alkyl group comprising 1 to 4 carbon atoms.Type: GrantFiled: December 20, 2001Date of Patent: January 14, 2003Assignee: E. I. du Pont de Nemours and CompanyInventors: Marie-Jose Lina, Eric Lacroix, Sophie Vanpoulle, Gerard Orcel, Robert Overton
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Publication number: 20030009062Abstract: 1Type: ApplicationFiled: July 12, 2002Publication date: January 9, 2003Inventors: Frank Dobert, Alexander Klausener, Paul Wagner
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Publication number: 20020189926Abstract: A process is disclosed for the purification, by distillation, of trimethylolpropane originating from the hydrogenation of 2,2-dimethylolbutanal, said process comprising the following steps:Type: ApplicationFiled: June 26, 2002Publication date: December 19, 2002Inventors: Matthias Dernbach, Detlef Kratz, Achim Stammer, Harald Rust, Gerhard Schulz
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Patent number: 6441254Abstract: The present invention relates to a process for preparing trimethylol compounds and formic acid by reaction of formaldehyde and aldehydes in the presence of a nitrogen base and distillation of the resulting reaction mixture in the presence of an auxiliary.Type: GrantFiled: December 13, 2001Date of Patent: August 27, 2002Assignee: Bayer AktiengesellschaftInventors: Frank Döbert, Paul Wagner, Alexander Klausener, Wolfgang Eymann, Rolf Feller
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Patent number: 6433192Abstract: In a process for preparing 1,4-butanediol, tetrahydrofuran and &ggr;-butyrolactone by oxidation of butane to give a product stream comprising maleic anhydride, absorption of maleic anhydride from the product stream using a high-boiling alcohol to give a liquid absorption product comprising monoesters and diesters of maleic acid and also high-boiling alcohol, after-esterification of the liquid absorption product and subsequent hydrogenation of the after-esterified product in the liquid phase, the high-boiling alcohol is a polyhydric alcohol having a boiling point at atmospheric pressure of above 233° C. and the after-esterified product has an acid number of less than 30 mg KOH/g and a water content of less than 1% by weight.Type: GrantFiled: June 4, 2001Date of Patent: August 13, 2002Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Gerd Kaibel, Rolf Pinkos, Ralf-Thomas Rahn
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Patent number: 6387033Abstract: LDH-osmate of the formula [MII(1−x)MIIIx(OH)2][OsO42−]x/2.zH2O wherein MII is a divalent cation selected from the group consisting of Mg2+, Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+ and Ca2+ and MIII is a trivalent ion selected from the group consisting of Al3+, Cr3+, Mn3+, Fe3+ and Co3+, and x is the mole fraction having integral value ranging from 0.2 to 0.33, and z is the number of water molecules and ranges from 1 to 4, useful as, a catalyst, and a process for the preparation thereof and use thereof to manufacture vicinal diols.Type: GrantFiled: November 22, 2000Date of Patent: May 14, 2002Assignee: Council of Scientific and Industrial ResearchInventors: Boyapati Manoranjan Choudary, Naidu Sreenivasa Chowdari, Mannepalli Lakshmi Kantam, Kondapuram Vijaya Raghavan, Chinta Venkat Reddy Reddy
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Patent number: 6376725Abstract: High purity 1,3-butylene glycol obtained from acetaldol by a liquid phase hydrogen reduction method, by adding a base to crude 1,3-butylene glycol free of high-boiling material, heat-treating the mixture and then distilling off 1,3-butylene glycol; and distilling off low-boiling materials from 1,3-butylene glycol. In high performance liquid chromatography analysis under specified conditions, each peak eluted in a relative retention time range of 4.0 to 5.5, taking a relative retention time of 1,3-butylene as 1.0, has an absorbance of 0.02 or less at a measuring wavelength of 210 nm. This has no odor and shows less change with time.Type: GrantFiled: July 6, 2000Date of Patent: April 23, 2002Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasuo Tsuji, Kunio Tagawa
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Patent number: 6369281Abstract: The present invention concerns a process for producing 2-butyl-2-ethyl-1,3-propanediol. According to the process, a reaction mixture is formed, containing 2-ethylhexanal and formaldehyde, into which an hydroxide compound is fed, whereby 2-ethylhexanal and formaldehyde are reacted to to produce 2-butyl-2-ethyl-1,3-propanediol. According to the invention, the hydroxide compound is incrementally fed into the reaction mixture. Preferably the hydroxide compound is fed at least at two input rates, in such a way that the heat production of the reaction between 2-ethylhexanal and formaldehyde immediately after each increase of the input rate of the hydroxide compound, is at least almost the same. The invention allows for the production of BEPD in a controlled and safe manner, with excellent yields.Type: GrantFiled: May 30, 2000Date of Patent: April 9, 2002Assignee: Neste OyjInventors: Lars-Peter Lindfors, Kalevi Heinola, Kari Kulmala, Hannele Hakanp{umlaut over (aa)}-Laitinen, Lea Rintala, Lea Parkkinen, Vesa-Matti Lehtinen
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Patent number: 6365789Abstract: The invention relates to a pulverulent sorbitol, characterized in that it exhibits a hygroscopicity value, determined according to a test A, of less than 2%, preferably of less than 1.7%, and a specific surface, determined according to the BET method, at least equal to 2 m2/g, preferably at least equal to 2.2 m2/g, and also relates to its process of preparation. The invention also relates to compositions intended in particular for the food and pharmaceutical fields and to the use of the said pulverulent sorbitol in the preparation of tablets exhibiting a <<smooth in the mouth>> texture.Type: GrantFiled: April 25, 2001Date of Patent: April 2, 2002Assignee: Roquette FreresInventors: Franck Moraly, Erik Labergerie, José Lis, Philippe Lefevre, Frédéric Bouvier
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Publication number: 20020033325Abstract: The present invention provides a process for recovering ditrimethylolpropane from a still residue obtained by extracting and then distilling off trimethylolpropane from a reaction solution obtained by reacting n-butyraldelhyde with formaldehyde in the presence of a basic catalyst, wherein the still residue is distilled to remove high-boiling components therefrom, and the resultant distillate is subjected to crystallization. When the above process is combined with the acid decomposition, it becomes possible to decompose a linear formal compound obtained from 2 molecules of TMP contained in the still residue as crude TMP and one molecule of formaldehyde, so that di-TMP having a higher purity is obtained.Type: ApplicationFiled: August 1, 2001Publication date: March 21, 2002Inventors: Teruyuki Ninomiya, Toshio Watanabe, Atsushi Iwamoto, Soemu Miyashita, Masafumi Watanabe
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Patent number: 6350923Abstract: A dialdehyde, trialdehyde or tetraldehyde or at least two thereof as aldehyde are hydrogenated by bringing into contact at least: the aldehyde; a catalyst comprising at least one metal selected from the group consisting of nickel, cobalt and copper in chemically bound and/or elemental form; hydrogen; at a gas pressure in the range from 5 to 350 bar and a temperature in the range from 40 to 300° C.Type: GrantFiled: December 28, 1999Date of Patent: February 26, 2002Assignee: BASF AktiengesellschaftInventors: Karsten Eller, Peter Wahl, Rolf Pinkos
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Patent number: 6344592Abstract: A method of producing a highly pure trimethylolpropane from a crude trimethylolpropane obtained by a reaction of n-butyl aldehyde and formaldehyde in the presence of a basic catalyst in a two-stage process of an aldol condensation and a crossed Cannizzaro reaction. Since a high-boiling component and an inorganic salt are removed in advance from the crude trimethylolpropane, hardly removable impurities such as condensation products in the crude trimethylolpropane are changed in the subsequent heat treatment under acidic conditions to components easily removable by distillation. By distilling the heat-treated crude trimethylolpropane, a highly pure trimethylolpropane with a low content of remaining formaldehyde and a low coloring degree is easily obtained.Type: GrantFiled: December 20, 1999Date of Patent: February 5, 2002Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Atsushi Iwamoto, Teruyuki Ninomiya, Toshio Watanabe, Takaki Ikebe
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Publication number: 20020010376Abstract: A method of producing a highly pure trimethylolpropane from a crude trimethylolpropane obtained by a reaction of n-butyl aldehyde and formaldehyde in the presence of a basic catalyst in a two-stage process of an aldol condensation and a crossed Cannizzaro reaction. Since a high-boiling component and an inorganic salt are removed in advance from the crude trimethylolpropane, hardly removable impurities such as condensation products in the crude trimethylolpropane are changed in the subsequent heat treatment under acidic conditions to components easily removable by distillation. By distilling the heat-treated crude trimethylolpropane, a highly pure trimethylolpropane with a low content of remaining formaldehyde and a low coloring degree is easily obtained.Type: ApplicationFiled: December 20, 1999Publication date: January 24, 2002Inventors: ATSUSHI IWAMOTO, TERUYUKI NINOMIYA, TOSHIO WATANABE, TAKAKI IKEBE
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Patent number: 6316679Abstract: A process for treating a composition containing a substantial proportion of trimethyflolpropane bis-monolinear formal (TMP-BMLF) or trimethylolethane bis-monolinear formal (TME-BMLF), e.g., a heavy ends residue obtained from the purification of a crude trimethylolpropane (TMP) or trimethylolethane (TME) product, wherein the composition is contacted at an elevated temperature with a strong acid catalyst, e.g., methanesulfonic acid, to produce a composition containing significantly increased amounts of TMP and trimethylolpropane monocyclic formal (TMP-MCF) or TME and trimethylolethane monocyclic formal (TME-MCF) respectively. Also disclosed is a process for reacting TMP-MCF or TME-MCF, either in substantially pure form or as present in the light ends overhead stream obtained in a finishing treatment of crude TMP or TME, with a monohydric or dihydric alcohol, e.g., ethylene glycol, in the presence of a strong acid catalyst to obtain additional TMP or TME and an acetal by-product, e.g.Type: GrantFiled: May 26, 2000Date of Patent: November 13, 2001Assignee: Celanese International CorporationInventors: Carolyn Supplee, Jerry A. Broussard, Tobin J. Marks, William E. Slinkard, Edwards G. Zey
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Patent number: 6294705Abstract: The invention relates to a method for producing alkali metal alcoholates by reacting alcohol with alkali metal in an aprotic, organic solvent in the presence of an H acceptor such as e.g. isoprene, butadiene, styrene or methyl styrene.Type: GrantFiled: February 6, 2001Date of Patent: September 25, 2001Assignee: Chemetall GmbHInventors: Ulrich Wietelmann, Uwe Lischka, Ute Emmel
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Patent number: 6288287Abstract: A process for preparing a glycerol from a crude glycerol comprising a glycerol, a diol and water, comprising feeding the crude glycerol to a preparation apparatus comprising two or more, serially connected flash towers and a distillation tower connected to a final flash tower, wherein a bottom fraction of each flash tower is fed to a subsequent flash tower; and adjusting an internal pressure of each flash tower to from 0.13 to 40 kPa, an internal temperature of each flash tower to 140° C. or less, a water content of the bottom fraction of the final flash tower to 0.1% by weight or less, and a pressure at bottom of the distillation tower to from 0.13 to 0.90 kPa.Type: GrantFiled: January 29, 2001Date of Patent: September 11, 2001Assignee: Kao CorporationInventors: Hideaki Ueoka, Takanobu Katayama
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Patent number: 6288286Abstract: A process for preparing 1,6-hexanediol from a carboxylic acid mixture obtained as by-product in the oxidation of cyclohexane to cyclohexanone/cyclohexanol with oxygen or oxygen-comprising gases and by aqueous extraction of the reaction mixture and comprising adipic acid, 6-hydroxycaproic acid and small amounts of 1,4-cyclohexanediols by esterification of the acids and hydrogenation, by a) reacting the mono- and dicarboxylic acids in the aqueous dicarboxylic acid mixture with a low molecular weight alcohol to form the corresponding carboxylic esters, b) conducting a first distillation to remove excess alcohol and low boilers from the esterification mixture obtained, c) conducting a second distillation to separate the bottom product into an ester fraction which is essentially free from 1,4-cyclohexanediols and a fraction which includes at least the larger proportion of the 1,4-cyclohexanediols, d) subjecting the ester fraction essentially free from 1,4-cyclohexanediols to a catalytic hydrogenation, and e)Type: GrantFiled: November 15, 2000Date of Patent: September 11, 2001Assignee: BASF AktiengesellschaftInventors: Frank Stein, Thomas Krug, Martin Gall, Gabriele Iffland
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Patent number: 6278030Abstract: An improved process for preparing alcohols by the Oxo process. More particularly this invention relates to an improvement in the hydrogenation step of the Oxo process characterized in the use of certain bulk multimetallic hydrogenation catalysts comprised of at least one Group VIII non-noble metal and at least two Group VIB metals.Type: GrantFiled: January 14, 2000Date of Patent: August 21, 2001Assignee: Exxon Chemical Patents, Inc.Inventors: Jose Manuel Vargas, Kenneth Lloyd Riley
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Patent number: 6274778Abstract: The invention relates to a pulverulent sorbitol, characterized in that it exhibits a hygroscopicity value, determined according to a test A, of less than 2%, preferably of less than 1.7%, and a specific surface, determined according to the BET method, at least equal to 2 m2/g, preferably at least equal to 2.2 m2/g, and also relates to its process of preparation. The invention also relates to compositions intended in particular for the food and pharmaceutical fields and to the use of the said pulverulent sorbitol in the preparation of tablets exhibiting a <<smooth in the mouth>> texture.Type: GrantFiled: December 9, 1999Date of Patent: August 14, 2001Assignee: Roquette FreresInventors: Franck Moraly, Erik Labergerie, José Lis, Philippe Lefevre, Frédéric Bouvier
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Patent number: 6268539Abstract: Method and apparatus for producing neopentyl glycol which comprises hydrogenating hydroxypivaldehyde in a reactor provided with a self-aspirator agitator device in the presence of a hydrogenation catalyst. The method has high yield of neopentyl glycol, and does not have to be carried out under high pressure as do certain prior art methods.Type: GrantFiled: October 7, 1999Date of Patent: July 31, 2001Assignee: Nan Ya Plastics CorporationInventors: Hsu Sen-Huang, Tsai Chia-Ruey, Chuang Jung-Jen
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Patent number: 6265624Abstract: A process is described for the continuous recovery of substantially pure pentane-1,5-diol from a crude product stream (1) containing pentane-1,5-diol and &dgr;-valerolactone. The feed stream (1) is continuously supplied to a vaporization zone (2) maintained under temperature and pressure conditions effective for the vaporization of pentane-1,5-diol and conducive to the thermal decomposition of reaction products of &dgr;-valerolactone thereby to form a vaporous stream. The resulting vaporous stream is continuously supplied to an intermediate section of a distillation zone (4). A reflux stream (5) of dimethyl glutarate is fed to an upper section of the distillation zone (4) and an overhead vapor product stream (8) comprising &dgr;-valerolactone and dimethyl glutarate is taken. Also an intermediate stream (11) comprising substantially pure pentane-1,5-diol is taken from the distillation zone (4), while from the bottom section of the distillation zone there is recovered a bottoms product (12).Type: GrantFiled: April 19, 2000Date of Patent: July 24, 2001Assignee: Kvaerner Process Technology, Ltd.Inventors: John Scarlett, Michael Anthony Wood, Paul Willett
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Patent number: 6265623Abstract: The reductive cleavage of linear and cyclic acetals, especially formals, in an aqueous medium containing a formate takes place by hydrogenation with hydrogen in the presence of a heterogeneous hydrogenation catalyst at a pH value of less than 7 at a temperature of over 200° C. The catalyst-poisoning effect of the formate is overcome at over 200° to 300° C., especially from over 200° to 280° C., so that, in a suspension procedure, the weight ratio of metal having hydrogenating activity to acetal is less than 0.1.Type: GrantFiled: August 26, 1999Date of Patent: July 24, 2001Assignee: Perstorp Specialty Chemicals ABInventors: Marcus Morawietz, Thomas Haas, Olaf Burkhardt, Rudolf Vanheertum
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Patent number: 6255540Abstract: A method for producing 2-substituted glycerols having various levels of hydroxy group protection by opening dihydroxyacetone dimer in a nonaqueous, non-protic environment with a composition that initially protects both of the liberated 1,3-dihydroxy groups to form di-ether containing ketone monomers which can then be conveniently subjected to ketone addition reactions and standard chemical functional group manipulations.Type: GrantFiled: June 28, 2000Date of Patent: July 3, 2001Assignee: The University of ToledoInventors: Paul W. Erhardt, Wieslaw A. Klis
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Patent number: 6235930Abstract: A process for the preparation of 3,4-dihydroxybutanoic acid (I) and 3-hydroxy-&ggr;-butyrolactone (V) thereof from a 3-leaving group substituted pentose source is described. In particular, the process relates to the synthesis of (R)-3,4-dihydroxybutanoic acid and (R)-3-hydroxy-&ggr;-butyrolactone from a 3-leaving group substituted L-pentose sugars. The process uses a base and a peroxide to convert the pentose source to the chiral 3,4-dihydroxybutanoic acid compound. The chiral 3,4-dihydroxybutanoic acid can be further converted to 3-hydroxy-&ggr;-butyrolactone by acidification. The chiral compound is useful as a chemical intermediate to the synthesis of various drugs and other products.Type: GrantFiled: March 31, 1999Date of Patent: May 22, 2001Assignee: Board of Trustees operating Michigan State UniversityInventor: Rawle I. Hollingsworth
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Patent number: 6207865Abstract: A carbonyl compound or a mixture of two or more carbonyl compounds is catalytically hydrogenated in the presence of a Raney copper catalyst in the form of nuggets.Type: GrantFiled: January 11, 2000Date of Patent: March 27, 2001Assignee: BASF AktiengesellschaftInventors: Boris Breitscheidel, Marc Walter, Detlef Kratz, Gerhard Schulz, Manfred Sauerwald
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Patent number: 6204417Abstract: In a process for preparing aliphatic alcohols by hydrogenating aliphatic carboxylic acids or anhydrides or esters thereof or lactones in the presence of a catalyst comprising Pt and Re, in the form of the metal or an oxide in each case, the catalyst further comprises at least one further element from the groups 5 to 12 and 14 and the lanthanides of the Periodic Table of the Elements in the form of the metal or an oxide.Type: GrantFiled: November 15, 1999Date of Patent: March 20, 2001Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Rolf Pinkos, Joachim Wulff-Döring
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Patent number: 6201159Abstract: A neopentyl glycol having a purity of 98% or more is produced continuously by a process comprising the steps of: conducting an aldol condensation of isobutyraldehyde with an aqueous formaldehyde solution containing methanol in an amount of 0.1 to 15 wt % in the presence of a tertiary alkylamine catalyst; extracting the condensation product mixture with octanol; distilling the extract; hydrogenating the distillation product; extracting the hydrogenation product mixture with water; and subjecting the extract to distillation.Type: GrantFiled: June 11, 1999Date of Patent: March 13, 2001Assignee: LG Chemical LimitedInventors: Jung-Uk Choi, Seong-Moon Jung, Kee-Hyouk Lee, Ji-Joong Moon, Young-Jin Kim, Kwang-Ik Moon
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Patent number: 6191320Abstract: In a process for finishing neopentyl glycol by cooling, crystallizing and comminuting a neopentyl glycol melt and subsequent packing of the resulting neopentyl glycol particles in storage or transport containers, the melt is cooled at the commencement of cooling for at least 1/10 minutes without use of a coolant or with use of a coolant having a temperature in the range from 50 to 120° C. and the product is packed at a temperature below 30° C.Type: GrantFiled: March 30, 2000Date of Patent: February 20, 2001Assignee: BASF AktiengesellchaftInventors: Stefan Käshammer, Andreas Klein, Charles L. Smith, Winfried Müller
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Patent number: 6187971Abstract: Methylolalkanal of the formula II (R=CH2OH, C1-C22-alkyl, aryl or C6-C22-aralkyl) is prepared spe-wise by a) reacting a C2-C24-aldehyde with formaldehyde in the presence of a tertiary amine, b) separating the reaction mixture i) into a bottom fraction comprising the compound of formula II and an incompletely methylolated compound of the formula III and a distillate stream comprising unconverted or partially converted starting materials, or ii) into an aqueous phase and an organic phase, and recycling the distillate stream or the organic phase to a), and c) subjecting the bottom fraction or the aqueous phase i) to a catalytic or thermal reaction to convert the compound of formula III to the compound of formula II and to a corresponding methylene compound of formula IV (R′=H or R) and ii) separating the reaction product into an overhead stream comprising the compound of formula IV and unconverted formaldehyde which is recycled to aType: GrantFiled: June 21, 1999Date of Patent: February 13, 2001Assignee: BASF AktiengesellschaftInventors: Detlef Kratz, Achim Stammer, Gerhard Schulz, Guido Voit
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Patent number: 6187970Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted 1,6-hexanediols which comprise subjecting one or more substituted or unsubstituted penten-1-ols to reductive hydroformylation in the presence of a reductive hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce said one or more substituted or unsubstituted 1,6-hexanediols. The substituted and unsubstituted 1,6-hexanediols produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., epsilon caprolactone. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted 1,6-hexanediols as principal product(s) of reaction.Type: GrantFiled: April 15, 1997Date of Patent: February 13, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John Robert Briggs, Diane Lee Packett, David Robert Bryant, Ailene Gardner Phillips, David James Schreck, Anil Sakharam Guram, Kurt Damar Olson, Thomas Carl Eisenschmid, Eric Bruce Tjaden
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Patent number: 6177597Abstract: A glycol solvent selected from a glycol and a tetramethylammonium carboxylate having improved dehydrating capacity and a reduced aborbency for aliphatic and aromatic hydrocarbons.Type: GrantFiled: July 6, 1999Date of Patent: January 23, 2001Assignee: Gavlin Associates, Inc.Inventors: Gilbert Gavlin, Boris Goltsin
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Patent number: 6172269Abstract: This invention relates to processes for producing one or more substituted or unsubstituted 1,6-hexanediols, e.g., 1,6-hexanediol, which comprise subjecting one or more substituted or unsubstituted alkadienes to hydrocarbonylation in the presence of a hydrocarbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted 1,6-hexanediols. The substituted and unsubstituted 1,6-hexanediols produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., epsilon caprolactone. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted 1,6-hexanediols as principal product(s) of reaction.Type: GrantFiled: April 15, 1997Date of Patent: January 9, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Anil Sakharam Guram, John Robert Briggs, Diane Lee Packett, Kurt Damar Olson, Thomas Carl Eisenschmid, Erik Bruce Tjaden
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Patent number: 6080896Abstract: A process for producing a polyhydric alcohol with high selectivity by subjecting formaldehyde and a specific aliphatic aldehyde to an aldol condensation reaction in the presence of a base catalyst, and then subjecting the resultant reaction product to a crossed Cannizzaro reaction, while reacting a solution containing a 2-substituted-2-alkanal, formed as a byproduct during the aldol condensation reaction, with water or formaldehyde in the presence of the base catalyst, and thereafter reacting the resultant mixture with the aliphatic aldehyde.Type: GrantFiled: April 29, 1999Date of Patent: June 27, 2000Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Teruyuki Ninomiya, Toshio Watanabe, Takaki Ikebe, Atsushi Iwamoto