Ethylenically Unsaturated Patents (Class 568/857)
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Patent number: 5811601Abstract: This invention relates to a process for the isomerization of a vinyl glycol to an unsaturated diol in the presence of a rhenium-based catalyst; and to a catalyst for said isomerization. More specifically, this invention relates to the isomerization of 3-butene-1,2-diol to 2-butene-1,4-diol; and to a process for the manufacture of 1,4-butanediol involving the step of isomerizing 3-butene-1,2-diol to 2-butene-1,4-diol in the presence of said catalyst. The catalyst is characterized in that it comprises a transition metal on a carrier wherein the carrier is a zeolite Y type substance containing silicon and aluminum in a mole ratio of from about 1.5:1 to about 1000:1, and the transition metal is rhenium or a rhenium compound and mixtures thereof present in an amount of from about 0.1 to about 50 weight percent based on total combined weight of the carrier and of the rhenium or rhenium compound and mixtures thereof.Type: GrantFiled: August 9, 1996Date of Patent: September 22, 1998Assignee: The Dow Chemical CompanyInventors: Thomas J. Remans, Pierre A. Jacobs, Johan Martens, Dominicus A. G. van Oeffelen, Mathias H. G. Steijns
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Patent number: 5731383Abstract: This invention relates to difunctional telechelic linear non-crosslinked polyolefins without pendant chain branched groups. The polyolefin compounds of this invention are useful for preparing high molecular weight polyesters, polyamides, polyureas and polyurethanes of high density without branching of the polymer chains, and with low permeability to gases and solvents.Type: GrantFiled: September 3, 1996Date of Patent: March 24, 1998Assignee: Amoco CorporationInventors: Philip O. Nubel, Howard B. Yokelson
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Patent number: 5728900Abstract: Catalyst and process for the preparation of butene-2-diol-1,4 by the hydrogenation of butyne-2-diol-1,4 in aqueous solution over a palladium-containing fixed-bed catalyst, which is doped with lead or cadmium, in which a catalyst is used which has been made by applying Pd and Pb or Pd and Cd successively, by vapor deposition or sputtering, to a metal gauze or a metal foil acting as support material followed by forming the catalyst at an elevated temperature in air.Type: GrantFiled: February 29, 1996Date of Patent: March 17, 1998Assignee: BASF AktiengesellschaftInventors: Franz Josef Brocker, Rainer Becker, Volkmar Menger, Peter Stops
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Patent number: 5714644Abstract: A process is disclosed for the selective hydrogenation of butynediol to 2-butene-1,4-diol using a palladium catalyst to which either copper and zinc, or silver and zinc, or copper, silver and zinc are added as doping agents. In the preferred embodiment, it has been possible, by optimizing the composition of the catalyst, to improve the activity and selectivity of the catalysts in question while also eliminating the need to handle toxic substances during the catalyst manufacturing process.Type: GrantFiled: March 20, 1997Date of Patent: February 3, 1998Assignee: BASF AktiengesellschaftInventors: Matthias Irgang, Volkmar Menger, Ernest Miesen, Peter Stops, Fritz Graf
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Patent number: 5559190Abstract: This invention relates to difunctional telechelic linear non-crosslinked polyolefins without pendant chain branched groups. The polyolefin compounds of this invention are useful for preparing high molecular weight polyesters, polyamides, polyureas and polyurethanes of high density without branching of the polymer chains, and with low permeability to gases and solvents.Type: GrantFiled: June 2, 1995Date of Patent: September 24, 1996Assignee: Amoco CorporationInventors: Philip O. Nubel, Howard B. Yokelson
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Patent number: 5530167Abstract: Disclosed is an improved process for the preparation of 1,4-butenediol by the hydrolysis of 3,4-epoxy-1-butene (EpB) wherein a mixture of EpB and water is contacted with a catalyst comprising a catalyst support material an copper in a positive valence state.Type: GrantFiled: August 21, 1995Date of Patent: June 25, 1996Assignee: Eastman Chemical CompanyInventor: Gerald C. Tustin
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Patent number: 5498734Abstract: The magnesium complexes of cyclic hydrocarbons containing conjugated dienes, such as 1,2-dimethylenecycloalkanes, and 1,3-butadienes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4 diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, alkylditriflates, bromoalkylnitriles, esters, or amides serve as a convenient method for synthesizing carbocyclic systems. Significantly, carbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4-diyl)magnesium complexes with carboxylic esters or acid halides whereas low temperatures lead to regioselective synthesis of .beta.,.gamma.-unsaturated ketones. Additionally, .gamma.Type: GrantFiled: July 30, 1993Date of Patent: March 12, 1996Assignee: University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5397810Abstract: The present invention relates to a novel polyol obtained by using a specified polyhydric alcohol, polyoxyalkylene polyol, aliphatic amine and/or alkamlamine as a raw material and adding an organic polycarboxylic acid or its anhydride and an alkylene oxide; a polyurethane resin prepared from said novel polyol and an organic polyisocyanate; a rigid polyurethane foam prepared by using a hydrochlorofluorocarbon or hydrofluorocarbon foaming agent which has very low public hazards; and a composite utilizing thereof.The production of rigid polyurethane foam by using the polyol of the invention can be carried out in good operation efficiency and low public hazards. Additionally, properties of the foam thus obtained is equivalent to those of rigid polyurethane foams obtained by using conventional chlorofluorocarbons. Consequently, the rigid polyurethane foam of the invention is very useful for insulation materials and structural insulation materials.Type: GrantFiled: February 19, 1993Date of Patent: March 14, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Satoshi Ozaki, Tsukuru Izukawa, Haruhiko Kawakami, Takayoshi Masuda, Masayuki Kimura, Toshio Nozawa, Masahiko Hashiba
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Patent number: 5336815Abstract: Preparation of vinyl glycols (I) ##STR1## (R.sup.1 to R.sup.6 =H, a carbo-organic radical, optionally substituted) in which an unsaturated diol of formula II ##STR2## is isomerized in the presence of a rhenium catalyst under neutral conditions. The compounds (I) serve as intermediates for the preparation of active substances and for the preparation of polymers.Type: GrantFiled: April 29, 1993Date of Patent: August 9, 1994Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Walter Gramlich, Michael Huellmann, Hans-Ulrich Scholz
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Patent number: 5324869Abstract: Acyclic terpene compounds useful as intermediates or producing sarcophytol A which have an anti-carcinogenic promotor activity and anti-tumor activity, which compounds are shown by the general formula (I): ##STR1##Type: GrantFiled: April 9, 1993Date of Patent: June 28, 1994Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5292907Abstract: The invention relates to a process for the manufacture of 6-trans-leukotriene B.sub.4 (LTB.sub.4) of formula ##STR1## in which a butadienediol is prepared; the hydroxyl groups are esterified to produce a diester and this diester is subjected to a stereospecific reductive elimination using low valency titanium [Ti(0)] to produce a 6-trans triether of formula: ##STR2## the groups --OA in positions 5 and 12 of which are then converted to --OH groups and the group --CH.sub.2 OA in position of which is then converted to a --COOH group, to produce 6-trans-LTB.sub.4.The invention also relates to intermediates obtained in the said manufacturing process.Type: GrantFiled: July 20, 1993Date of Patent: March 8, 1994Assignee: L'OrealInventors: Jean Maignan, Guy Solladie, Guy Stone
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Patent number: 5264638Abstract: A process for the extraction and purification of the diterpene alcohol Plaunotol from the leaves of the medicinal plant, Croton sublyratus Kurz. The process involves extracting firstly with a lower aliphatic alcohol followed by extracting from the alcohol solution with a chlorinated hydrocarbon. Then impurities are hydrolysed and the required Plaunotol separated by extraction with a hydrocarbon. This process is simple and gave much better yields than prior processes.Type: GrantFiled: January 28, 1992Date of Patent: November 23, 1993Assignee: Chulalongkorn UniversityInventor: Naline Nilubol
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Patent number: 5260495Abstract: The invention relates to highly selective, heterogeneous hydrotalcite-type catalysts for the production of monoalkylene glycol by hydrolysis of the corresponding alkylene oxide. The invention also relates to method of preparing these catalysts using large organic anion spacers, and a process for producing monoalkylene glycol.Type: GrantFiled: August 4, 1992Date of Patent: November 9, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Matthew W. Forkner
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Patent number: 5216181Abstract: Liquid telechelic polymers are made from dienes and are produced via anionic polymerization. While having low molecular weight, for example less than 15,000, the telechelic polymers are generally gel-free, have high amounts of trans-1,4 structure, low vinyl unsaturation and low bulk viscosities. The liquid telechelic polymers are made utilizing a trimetallic initiator comprised of (1) an organopolylithium compound and (2) a complex of a trialiphatic substituted aluminum compound or derivative thereof and a barium salt of an organic alcohol.Type: GrantFiled: August 26, 1991Date of Patent: June 1, 1993Assignee: GenCorp Inc.Inventors: I. Glen Hargis, Hubert J. Fabris, John A. Wilson, Russell A. Livigni
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Patent number: 5149843Abstract: Conjugated diene compounds of the general formula: ##STR1## which are industrially advantageous intermediates for preparing sarcophytol A useful as an anticarcinogenic promotor or antitumor agent are provided.Type: GrantFiled: June 7, 1991Date of Patent: September 22, 1992Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5126268Abstract: A process is disclosed for the isolation of an enantiomerically enriched alcohol from a first mixture of an enantiomerically enriched 1-arylsulfonate-2 -hydroxy-3-butene and an enantiomerically enriched 1 -arylsulfonate- 2-acyloxy-3-butene. The process includes the steps of:(a) contacting the mixture with a reagent capable of reacting with said 1-arylsulfonate-2-hydroxy-3-butene to remove the arylsulfonate group and produce a mixture of dihydroxybutene monoesters thereby forming a second mixture containing said dihydroxybutene monoesters and unreacted enantiomerically enriched 1-arylsulfonate-2-acyloxy-3-butene(b) contacting the second mixture with reagents capable of hydrolyzing all of the acyl groups in said mixture to hydroxy groups so as to produce a third mixture comprising 1,2-dihydroxy-3-butenes and enantiomerically enriched 1-arylsulfonate-2-hydroxy-3 -butene;(c) washing said third mixture with water so as to remove said 1,2-dihydroxy-3-butenes.Type: GrantFiled: February 26, 1991Date of Patent: June 30, 1992Assignee: Eastman Kodak CompanyInventor: Neil W. Boaz
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Patent number: 5126267Abstract: A process is disclosed for the isolation of an enantiomerically enriched alcohol from a first mixture of an enantiomerically enriched alcohol and an enantiomerically enriched ester. The process includes the steps of:(a) contacting the mixture with a reagent capable of reacting with the hydroxy function of the alcohol, without the loss of optical purity, so as to produce a second mixture containing a base stable derivative of the enantiomerically enriched alcohol and the unreacted ester;(b) contacting the second mixture with a base capable of reacting with the ester so as to produce a third mixture containing a compound more volatile than the base stable derivative of the alcohol;(c) removing the volatile compound from the third mixture; and(d) converting the base stable derivative of the alcohol back to the enantiomerically enriched alcohol, without the loss of optical purity.Type: GrantFiled: February 26, 1991Date of Patent: June 30, 1992Assignee: Eastman Kodak CompanyInventor: Neil W. Boaz
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Patent number: 5118882Abstract: Novel streptenols with pharmacological activity, in particular with HMG-CoA-reductase inhibiting activity, can be isolated from the nutrient broth of streptomycetes. These compounds can also be used as synthesis unit for the production of mevilonin analogues.Type: GrantFiled: February 22, 1990Date of Patent: June 2, 1992Assignee: Hoechst AktiengesellschaftInventors: Axel Zeeck, Susanne Grabley, Joachim Wink, Peter Hammann, Carlo Giani, Pia Kricke-Helling
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Patent number: 5081311Abstract: Muscone of the formula I ##STR1## is prepared by a process in which an open-chain 2,15-diketone of the general formula IICH.sub.3 --CO--X--CO--CH.sub.3 (II)where X is one of the radicals--(--CH.sub.2 --).sub.12 -- (a)--CH.dbd.CH--(--CH.sub.2 --).sub.8 --CH.dbd.CH-- (b)--CH.sub.2 --CH.dbd.CH--(--CH.sub.2 --).sub.6 --CH.dbd.CH--CH.sub.2 --(c)--CH.sub.2 --CH.sub.2 --CH.dbd.CH--(--CH.sub.2 --).sub.4 --CH.dbd.CH--CH.sub.2 --CH.sub.2 -- (d) or--CH.sub.2 --CH.sub.2 CH.sub.2 --CH.dbd.CH--(--CH.sub.2 --).sub.2 --CH.dbd.CH--CH.sub.2 --CH.sub.2 --CH.sub.2 -- (e)is brought into contact, at from 300.degree. to 400.degree. C. in the presence of from 5 to 15% by weight, based on the amount of catalyst, of water, in the gas phase, with a fixed-bed catalyst containing TiO.sub.2, CeO.sub.2 or the ThO.sub.2 as the catalytically active compound and the unsaturated cyclic ketone formed by intramolecular aldol condensation is subjected to catalytic hydrogenation.Type: GrantFiled: May 18, 1990Date of Patent: January 14, 1992Assignee: BASF AktiengesellschaftInventors: Michael Huellmann, Thomas Kuekenhoehner, Karl Brenner, Rainer Becker, Matthias Irgang, Charles Schommer
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Patent number: 5053561Abstract: A method of isolating trans-1,1,4,4-tetraalkyl-2-butene-1,4-diols of formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and denote C.sub.1 - to C.sub.5 -alkyl, from mixtures thereof with their cis-isomers, wherein the trans-isomer is separated from the cis-isomer by liquid-liquid extraction.Type: GrantFiled: June 13, 1990Date of Patent: October 1, 1991Assignee: BASF AktiengesellschaftInventors: Dietmar Bender, Klaus Bronstert, Martin Fischer, Gregor Schuermann
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Patent number: 5043484Abstract: Disclosed is an improvement in a process for polymerizing 1,3-butadiene selectively to form relatively low molecular weight hydroxyl-terminated polybutadiene oligomers in the presence of an aqueous solution of hydrogen peroxide which comprises the use of a glycol ether solvent to produce butadiene oligomers having a high degree of OH functionality and suppression of formation of solid or gel-type insoluble rubber by-products.Type: GrantFiled: February 9, 1990Date of Patent: August 27, 1991Assignee: Texaco Chemical CompanyInventors: John F. Knifton, Edward T. Marquis
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Patent number: 5030739Abstract: The invention is directed to a process for the catalytic oxidation of an isoprenoid containing at least one allylic hydrogen atom, which process comprises reacting the isoprenoid with oxygen or an oxygen-containing gas in an inert solvent in the presence of a N-hydroxydicarboxylic acid imide of the formula ##STR1## wherein A-B stands for CH.sub.2 -CH.sub.2, CH.dbd.CH, an aromatic hydrocarbon residue or a group derived from one of these groups in which one or more hydrogen atoms is/are replaced by alkyl or halogen,to produce a primary of secondary hydroperoxide.The process of the invention is suitable for the manufacture of steroids, vitamins, odorant substances, carotinoids and the like.Type: GrantFiled: August 31, 1990Date of Patent: July 9, 1991Assignee: Hoffman-La Roche Inc.Inventors: Joseph Foricher, Claude Furbringer, Karlheinz Pfoertner
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Patent number: 4990697Abstract: A process for producing homoallyl alcohols of the general formula (I) ##STR1## in which either A.sup.1 or A.sup.3 represents a hydrogen atom, the other represents a single bonding along with A.sup.2 ; R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different and independently represents a hydrogen atom, or an alkyl or alkenyl group with or without being substituted with a hydroxyl group or an akoxyl group; and Y represents a hydrogen atom, an alkyl group or an alkenyl group, by reacting 1,3-glycols of the general formula (II) ##STR2## in which X and Y are the same or different and independently represents a hydrogen atom, an alkyl group or an alkenyl group, R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 independently represents as defined above, at a temperature in the range of 130.degree. to 250.degree. C. in liquid phase with the contact of .gamma.-alumina catalyst.Type: GrantFiled: October 16, 1989Date of Patent: February 5, 1991Assignee: Kuraray Co., Ltd.Inventors: Tsumoru Renge, Osamu Yamada, Katumi Omura
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Patent number: 4982021Abstract: Alkylene glycols are produced by the reaction of alkylene oxide with water in the presence of a metalate-containing solid wherein the metalate is in association with electropositive complexing sites on a solid support such as an anion exchange resin.Type: GrantFiled: June 8, 1988Date of Patent: January 1, 1991Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventors: Robert D. Best, Joseph A. Collier, Brian T. Keen, John H. Robson
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Patent number: 4967018Abstract: A process for the catalytic hydrolysis of alkylene oxide to alkylene glycol using a hydrothermally stable, mixed metal framework catalyst composition selected from(a) material having the formulaM.sub.x.sup.2+ Q.sub.y.sup.3+ (OH) 2x+3y-nz A.sub.z.sup.n-. a 1 H.sub.2 O (I)wherein M is at least one divalent metal cation; Q is at least one trivalent metal cation; and A is at least one anion providing a valence (n.sup.31), wherein n is at least 1, and wherein a is a positive number, M, Q, and A are provided in a proportion such that x/y is a number equal to or greater than 1, z has a value greater than zero and 2x+3y-nz is a positive number, and M, Q and A are selected to provide a layered structure, and(b) material prepared by calcining the material of formula (I) having the formulaM.sub.x.sup.2+ Q.sub.y.sup.3+ (O).sub.(2x+3y-nz)/2D.sub.z.sup.n-(II)wherein M, Q, x, y, z and n have the same meanings defined above in connection with formula (I) and D is at least one nonvolatile anion.Type: GrantFiled: October 18, 1989Date of Patent: October 30, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventors: Hwaili Soo, Bernard C. Ream, John H. Robson
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Patent number: 4960754Abstract: Described are 3,7-dimethyl-6,7-dioxo-1,3-octadienes or mixtures of same defined according to the structure: ##STR1## wherein R is hydrogen or ethyl and X is one of the moieties: ##STR2## and wherein the wavy lines represent a "E" or "Z" configuration of the methyl and vinyl moiety about the 3,4-pi-bond of the molecule, as well as methods for methods for augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles by adding thereto an aroma augmenting or enhancing quantity of at least one of said 3,7-dimethyl-6,7-dioxo-1,3-octadienes.Type: GrantFiled: December 8, 1989Date of Patent: October 2, 1990Assignee: International Flavors & Fragrances Inc.Inventors: Richard A. Wilson, Michael J. Zampino, Braja D. Mookherjee, Robert W. Trenkle, Anton Van Ouwerkerk, Myrna L. Hagedorn, Michael G. Monteleone
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Patent number: 4943397Abstract: The present invention relates to a process for metathesizing an olefin having at least one terminal functional group which comprises contacting said olefin at metathesis conditions with a catalyst comprising: (a) a transition metal selected from tungsten, molybdenum and rhenium, (b) an organometallic compound based on an element selected from aluminum, tin, lead, magnesium and titanium, and (c) an oxophilic agent having a metal-oxygen bond strength greater than the metal-oxygen bond strength of said transition metal.Type: GrantFiled: September 22, 1988Date of Patent: July 24, 1990Assignee: Shell Oil CompanyInventor: Thomas H. Johnson
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Patent number: 4943396Abstract: The present invention relates to a process for preparing linear alpha, omega difunctional molecules by a process which comprises isomerizing olefins having at least one terminal functional group to form a mixture of functionalized olefinic isomers and metathesizing said functionalized olefinic isomers to produce a mixture of difunctional molecules and internal olefins.Type: GrantFiled: September 22, 1988Date of Patent: July 24, 1990Assignee: Shell Oil CompanyInventor: Thomas H. Johnson
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Patent number: 4924026Abstract: Described are triisobutylene alcohols and esters and halogenated intermediates for preparing same defined according to the generic structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; wherein R.sub.1 " and R.sub.2 " are the same or different and each represents hydrogen, chloro, bromo, hydroxyl or a C.sub.1 -C.sub.3 acyloxy with the provisos that when the dashed line in the 4--4' position is a carbon-carbon double bond then R.sub.1 " is hydrogen and R.sub.2 " is not hydrogen, and R.sub.1 " and R.sub.2 " are not both hydrogen.Also described are the uses of the triisobutylene alcohols and esters in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to perfumed polymers solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations.Type: GrantFiled: August 11, 1989Date of Patent: May 8, 1990Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, Marie R. Hanna
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Patent number: 4827004Abstract: Novel Isoprene Derivatives which have mucosa-protective and gastric acid secretion-inhibiting properties and are useful for combatting ulcers both by treating and as a prophylaxis against gastric and/or duodenal ulcers.Type: GrantFiled: August 24, 1987Date of Patent: May 2, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Albert Fischli, Max Schmid, Rudolf Schmid
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Patent number: 4801759Abstract: A method for the continuous saponification of epoxides with 3-8 carbon atoms at low pressures, preferably atmospheric pressure, and low boiling temperatures with small amounts of water. Yields and selectivities are very high.Type: GrantFiled: August 7, 1987Date of Patent: January 31, 1989Assignee: Degussa AktiengesellschaftInventors: Rainer Siegmeier, Gu Prescher, Helmut Maurer
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Patent number: 4772727Abstract: A multistage method for producing R-(+)-.alpha.-lipoic acid and S-(-)-.alpha.-lipoic acid (thioctic acid) by reacting a compound of formula II ##STR1## by means of enantioselective epoxidation to the epoxy alcohol of formula III, ##STR2## reduction to 1,3-diol-dihydroxynone-8-ene of formula IV, ##STR3## reaction with a substituted sulfonic acid chloride to 1,3-disulfoxynone-8-ene of formula V, ##STR4## oxidation with ruthenium tetroxide to 6,8-disulfoxyoctanoic acid of formula VI ##STR5## and subsequent reaction with sodium sulfide/sulfur.Type: GrantFiled: August 7, 1987Date of Patent: September 20, 1988Assignee: DegussaInventors: Ian O. Sutherland, Philip C. B. Page, Christopher M. Rayner
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Patent number: 4760200Abstract: The process for the liquid-phase hydration of a vicinal alkylene oxide(s) to the corresponding alkylene glycol(s) comprising carrying out such hydration in an aqueous medium containing a water miscible alkylene glycol ether co-solvent.Type: GrantFiled: December 31, 1985Date of Patent: July 26, 1988Assignee: Union Carbide CorporationInventors: Brian T. Keen, John H. Robson, George E. Keller, II
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Patent number: 4701571Abstract: An improved process for the hydrolysis of alkylene oxide to produce alkylene glycol which comprises:(a) reacting alkylene oxide and water in the presence of a selectivity-enhancing metalate-containing solid until about 90-95% of the alkylene oxide is converted to alkylene glycol; and(b) completing the hydrolysis reaction of (a) in the absence of the selectivity-enhancing metalate-containing solid.Type: GrantFiled: June 30, 1986Date of Patent: October 20, 1987Assignee: Union Carbide CorporationInventors: Hwaili Soo, John H. Robson
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Patent number: 4661646Abstract: 1-Butene-3,4-diol is prepared by heat treatment of 2-butene-1,4-diol in the presence of catalytically active substances under acid conditions.Type: GrantFiled: November 21, 1985Date of Patent: April 28, 1987Assignee: Bayer AktiengesellschaftInventors: Rolf Schalenbach, Helmut Waldmann
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Patent number: 4644085Abstract: The invention relates to a new anti-cancer chemical compound which has been called rooperol and certain derivatives thereof of the general formula ##STR1## in which A is chosen from the group including a phenyl group, a substituted phenyl group and --CH.sub.2 --O--R.sup.5 where R.sup.5 =H, an alkyl (C.sub.1 -C.sub.5), aralkyl or acyl substituent; R.sup.1 and R.sup.2 are chosen from substituents including H for both or singly if one of them is --OH, --NH.sub.2, --SH, ##STR2## or taken together R.sup.1 and R.sup.2 are =0; R.sup.3 is H or ##STR3## where R.sup.6 is an alkyl group (C.sub.1 -C.sub.7); either of R.sup.4 or B are chosen from substituents including H, ##STR4## a phenyl group, substituted phenyl group or a furyl group.Type: GrantFiled: June 4, 1985Date of Patent: February 17, 1987Assignee: Rooperol (NA) NVInventors: Siegfried Drewes, Roelof W. Liebenberg
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Patent number: 4626603Abstract: Aliphatic or cyclic epoxides containing 3 to 8 carbon atoms which are present in aromatic hydrocarbons or halohydrocarbons are saponified continuously and directly to vicinal diols without the use of high temperatures and pressures which would otherwise be necessary. The saponification is acid catalyzed.Type: GrantFiled: November 15, 1985Date of Patent: December 2, 1986Assignee: Degussa AktiengesellschaftInventors: Rainer Siegmeier, Gunter Prescher, Helmut Maurer
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Patent number: 4626604Abstract: A continuous multi-stage hydrogenation process is described.This is effected in at least three catalytic stages connected in series. All stages up to and including the penultimate stage are operated adiabatically and in the vapor phase. Aldehyde (or other unsaturated organic compound) is fed to all stages up to and including the penultimate stage. The rate of supply of the aldehyde or other unsaturated organic compound to the penultimate stage is controlled in relation to the catalyst volume in the penultimate catalytic stage so that the degree of hydrogenation in that stage is less than 100%. The remaining chemically unsaturated material in the product mixture from the penultimate stage is hydrogenated, after cooling that product mixture, in the final catalytic stage to produce a substantially completely hydrogenated product mixture. In this way the dwell time of the reactants and product(s) at "hot spot" temperatures is minimized, thus reducing byproduct formation.Type: GrantFiled: September 11, 1985Date of Patent: December 2, 1986Assignee: Davy McKee (London) LimitedInventors: Andrew G. Hiles, John E. Logsdon
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Patent number: 4579982Abstract: Alkylene oxides are hydrolyzed in a reaction menstruum containing an aqueous phase, a water-immiscible liquid phase, and a selectivity-enhancing, dissociatable metalate anion-containing material. The concentration of the metalate anion-containing material is greater in the water-immiscible liquid phase than that in the aqueous phase. The water-immiscible liquid phase can be separated from the aqueous phase to recover metalate anion-containing material.Type: GrantFiled: March 28, 1984Date of Patent: April 1, 1986Assignee: Union Carbide CorporationInventors: John R. Briggs, John H. Robson
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Patent number: 4579983Abstract: In processes for the hydrolysis of alkylene oxide to form alkylene glycols in the presence of selectivity-enhancing organometalate wherein the organometalate is provided in a water-insoluble phase, a stabilizing material is used to enhance the stability of the organometalate. The stabilizing material is water-soluble and comprises a cation and a selectivity-enhancing metalate anion.Type: GrantFiled: March 28, 1984Date of Patent: April 1, 1986Assignee: Union Carbide CorporationInventor: Brian T. Keen
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Patent number: 4578524Abstract: The process for the liquid-phase hydration of a vicinal alkylene oxide(s) to the corresponding alkylene glycol(s) comprising carrying out such hydration in the presence of vanadate anion and a selectivity-enhancing amount of carbon dioxide.Type: GrantFiled: March 28, 1984Date of Patent: March 25, 1986Assignee: Union Carbide CorporationInventor: Brian T. Keen
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Patent number: 4571440Abstract: A continuous process for making alkylene glycols by the hydrolysis of alkylene oxides in the presence of selectivity-enhancing organometalate wherein the alkylene glycol-containing hydrolysis product contains organometalate comprises recovering organometalate by extraction with a water-immiscible solvent, separating the resulting organometalate-containing solvent into an organometalate-lean stream for reuse in the extraction and an organometalate-rich stream for reuse in the hydrolysis.Type: GrantFiled: October 23, 1984Date of Patent: February 18, 1986Assignee: Union Carbide CorporationInventors: Brian T. Keen, John H. Robson
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Patent number: 4564715Abstract: High selectivity to monoalkylene glycol is obtained by contacting in an associated moiety-forming zone alkylene oxide and a selectivity enhancing, dissociatable metalate anion under conditions sufficient to associate at least a portion of the alkylene oxide with metalate anion, and then contacting the associated moiety with water in a glycol-forming zone to form alkylene glycol. The alkylene glycol can be separated from metalate anion. Desirably, the metalate anion can be recycled to the associated moiety-forming zone.Type: GrantFiled: October 23, 1984Date of Patent: January 14, 1986Assignee: Union Carbide CorporationInventors: John R. Briggs, George L. O'Connor, John H. Robson
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Patent number: 4560813Abstract: In processes for making alkylene glycols by the hydrolysis of alkylene oxides in the presence of selectivity-enhancing metalate anion-containing material, metalate anion can be recovered from the alkylene glycol-containing hydrolysis product by contact with a solid having electropositive complexing sites thereon such as anion exchange resins.Type: GrantFiled: March 28, 1984Date of Patent: December 24, 1985Assignee: Union Carbide CorporationInventor: Joseph A. Collier
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Patent number: 4551566Abstract: The process for the liquid-phase hydration of a vicinal alkylene oxide(s) to the corresponding alkylene glycol(s) comprising carrying out such hydration in the presence of a vanadate salt wherein the pH of the liquid phase is between about 5 and 12.Type: GrantFiled: September 8, 1983Date of Patent: November 5, 1985Assignee: Union Carbide CorporationInventors: John H. Robson, George E. Keller, II
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Patent number: 4536347Abstract: Ruthenium-on-charcoal and ruthenium-on-carbon black catalysts, containing from 0.1 to 5% by weight of iron, for the preparation of olefinically unsaturated alcohols by selective hydrogenation of the corresponding .alpha., .beta.-unsaturated carbonyl compounds in the liquid phase are prepared by modifying the catalyst with iron only after it has been impregnated with the ruthenium compound, and reducing the catalyst with hydrogen at from 400.degree. to 600.degree. C., with thorough mixing.The catalysts according to the invention are particularly useful for improving the industrially difficult hydrogenation of citral to give the soughtafter fragrances geraniol and nerol.Type: GrantFiled: March 19, 1984Date of Patent: August 20, 1985Assignee: BASF AktiengesellschaftInventors: Michael Horner, Matthias Irgang
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Patent number: 4500463Abstract: Polyprenyl carboxylic acid derivatives having the general formula (I): ##STR1## in which n is an integer of from 2 to 4, R.sub.1 represents the hydrogen atom or a protecting group for the carboxylic acid group, and R.sub.2 represents a hydroxymethyl, formyl or carboxyl group, are disclosed. A process for the preparation of the polyprenyl carboxylic acid derivative involving microbiological oxidation using a strain belonging to the genus Nocardia is disclosed. The compounds have anti-ulcer activity and hypotensive activity. The compounds also are useful as intermediates for preparing polyprenyl carboxylic acids of the formula ##STR2## and esters thereof, wherein l is an integer of from 4 to 11. The polyprenyl carboxylic acids and esters thereof have hypotensive activity and anti-ulcer activity.Type: GrantFiled: May 1, 1981Date of Patent: February 19, 1985Assignees: Eisai Co., Ltd., Agency of Industrial Science & TechnologyInventors: Akio Sato, Kenji Nakajima, Yoshimasa Takahara, Shizumasa Kijima, Yuichi Inai, Yoshiyuki Kohara, Yoshiyuki Kawakami, Tomio Tsurugi
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Patent number: 4480123Abstract: A process for preparing diacyloxyalkadienes of the formula ##STR1## where R.sup.1 to R.sup.6 are each hydrogen or a hydrocarbon radical, which contain one or more hydrocarbon radicals having one or more non-conjugated double bonds, by reacting an aliphatic triene of the formula ##STR2## in which R.sup.1 to R.sup.6 have the same meanings given above with a carboxylic acid of the formulaR.sup.7 -COOHin which R.sup.7 has the same meaning given above, in the presence of a catalyst which contains palladium, platinum or salts of these metals and in the presence of oxygen.Type: GrantFiled: July 25, 1983Date of Patent: October 30, 1984Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Hans-Martin Weitz
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Patent number: 4436940Abstract: Low molecular weight olefin polymers and copolymers of 3-butene-1-ol of molecular weights within range of from about 200 to about 4000.Type: GrantFiled: April 21, 1981Date of Patent: March 13, 1984Assignee: Standard Oil Company (Indiana)Inventors: Ellis K. Fields, William C. Clarke
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Patent number: 4429139Abstract: Rose oxide, or 2-[2-methyl-prop-l-en-l-yl]-4-methyl-tetrahydropyrane, a fragrant chemical specialty, is prepared efficiently by a novel process which consists in five reaction steps and uses citronellol as starting material.Type: GrantFiled: October 19, 1982Date of Patent: January 31, 1984Assignee: Firmenich SAInventor: Charles Fehr