Ethylenically Unsaturated Patents (Class 568/857)
  • Patent number: 5811601
    Abstract: 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: Grant
    Filed: August 9, 1996
    Date of Patent: September 22, 1998
    Assignee: The Dow Chemical Company
    Inventors: Thomas J. Remans, Pierre A. Jacobs, Johan Martens, Dominicus A. G. van Oeffelen, Mathias H. G. Steijns
  • Patent number: 5731383
    Abstract: 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: Grant
    Filed: September 3, 1996
    Date of Patent: March 24, 1998
    Assignee: Amoco Corporation
    Inventors: Philip O. Nubel, Howard B. Yokelson
  • Patent number: 5728900
    Abstract: 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: Grant
    Filed: February 29, 1996
    Date of Patent: March 17, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Josef Brocker, Rainer Becker, Volkmar Menger, Peter Stops
  • Patent number: 5714644
    Abstract: 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: Grant
    Filed: March 20, 1997
    Date of Patent: February 3, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Irgang, Volkmar Menger, Ernest Miesen, Peter Stops, Fritz Graf
  • Patent number: 5559190
    Abstract: 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: Grant
    Filed: June 2, 1995
    Date of Patent: September 24, 1996
    Assignee: Amoco Corporation
    Inventors: Philip O. Nubel, Howard B. Yokelson
  • Patent number: 5530167
    Abstract: 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: Grant
    Filed: August 21, 1995
    Date of Patent: June 25, 1996
    Assignee: Eastman Chemical Company
    Inventor: Gerald C. Tustin
  • Patent number: 5498734
    Abstract: 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: Grant
    Filed: July 30, 1993
    Date of Patent: March 12, 1996
    Assignee: University of Nebraska
    Inventor: Reuben D. Rieke
  • Patent number: 5397810
    Abstract: 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: Grant
    Filed: February 19, 1993
    Date of Patent: March 14, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Satoshi Ozaki, Tsukuru Izukawa, Haruhiko Kawakami, Takayoshi Masuda, Masayuki Kimura, Toshio Nozawa, Masahiko Hashiba
  • Patent number: 5336815
    Abstract: 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: Grant
    Filed: April 29, 1993
    Date of Patent: August 9, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Walter Gramlich, Michael Huellmann, Hans-Ulrich Scholz
  • Patent number: 5324869
    Abstract: 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: Grant
    Filed: April 9, 1993
    Date of Patent: June 28, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 5292907
    Abstract: 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: Grant
    Filed: July 20, 1993
    Date of Patent: March 8, 1994
    Assignee: L'Oreal
    Inventors: Jean Maignan, Guy Solladie, Guy Stone
  • Patent number: 5264638
    Abstract: 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: Grant
    Filed: January 28, 1992
    Date of Patent: November 23, 1993
    Assignee: Chulalongkorn University
    Inventor: Naline Nilubol
  • Patent number: 5260495
    Abstract: 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: Grant
    Filed: August 4, 1992
    Date of Patent: November 9, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Matthew W. Forkner
  • Patent number: 5216181
    Abstract: 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: Grant
    Filed: August 26, 1991
    Date of Patent: June 1, 1993
    Assignee: GenCorp Inc.
    Inventors: I. Glen Hargis, Hubert J. Fabris, John A. Wilson, Russell A. Livigni
  • Patent number: 5149843
    Abstract: 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: Grant
    Filed: June 7, 1991
    Date of Patent: September 22, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 5126268
    Abstract: 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: Grant
    Filed: February 26, 1991
    Date of Patent: June 30, 1992
    Assignee: Eastman Kodak Company
    Inventor: Neil W. Boaz
  • Patent number: 5126267
    Abstract: 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: Grant
    Filed: February 26, 1991
    Date of Patent: June 30, 1992
    Assignee: Eastman Kodak Company
    Inventor: Neil W. Boaz
  • Patent number: 5118882
    Abstract: 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: Grant
    Filed: February 22, 1990
    Date of Patent: June 2, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Axel Zeeck, Susanne Grabley, Joachim Wink, Peter Hammann, Carlo Giani, Pia Kricke-Helling
  • Patent number: 5081311
    Abstract: 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: Grant
    Filed: May 18, 1990
    Date of Patent: January 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Huellmann, Thomas Kuekenhoehner, Karl Brenner, Rainer Becker, Matthias Irgang, Charles Schommer
  • Patent number: 5053561
    Abstract: 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: Grant
    Filed: June 13, 1990
    Date of Patent: October 1, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Dietmar Bender, Klaus Bronstert, Martin Fischer, Gregor Schuermann
  • Patent number: 5043484
    Abstract: 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: Grant
    Filed: February 9, 1990
    Date of Patent: August 27, 1991
    Assignee: Texaco Chemical Company
    Inventors: John F. Knifton, Edward T. Marquis
  • Patent number: 5030739
    Abstract: 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: Grant
    Filed: August 31, 1990
    Date of Patent: July 9, 1991
    Assignee: Hoffman-La Roche Inc.
    Inventors: Joseph Foricher, Claude Furbringer, Karlheinz Pfoertner
  • Patent number: 4990697
    Abstract: 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: Grant
    Filed: October 16, 1989
    Date of Patent: February 5, 1991
    Assignee: Kuraray Co., Ltd.
    Inventors: Tsumoru Renge, Osamu Yamada, Katumi Omura
  • Patent number: 4982021
    Abstract: 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: Grant
    Filed: June 8, 1988
    Date of Patent: January 1, 1991
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: Robert D. Best, Joseph A. Collier, Brian T. Keen, John H. Robson
  • Patent number: 4967018
    Abstract: 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: Grant
    Filed: October 18, 1989
    Date of Patent: October 30, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: Hwaili Soo, Bernard C. Ream, John H. Robson
  • Patent number: 4960754
    Abstract: 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: Grant
    Filed: December 8, 1989
    Date of Patent: October 2, 1990
    Assignee: 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
  • Patent number: 4943397
    Abstract: 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: Grant
    Filed: September 22, 1988
    Date of Patent: July 24, 1990
    Assignee: Shell Oil Company
    Inventor: Thomas H. Johnson
  • Patent number: 4943396
    Abstract: 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: Grant
    Filed: September 22, 1988
    Date of Patent: July 24, 1990
    Assignee: Shell Oil Company
    Inventor: Thomas H. Johnson
  • Patent number: 4924026
    Abstract: 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: Grant
    Filed: August 11, 1989
    Date of Patent: May 8, 1990
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, Marie R. Hanna
  • Patent number: 4827004
    Abstract: 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: Grant
    Filed: August 24, 1987
    Date of Patent: May 2, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Albert Fischli, Max Schmid, Rudolf Schmid
  • Patent number: 4801759
    Abstract: 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: Grant
    Filed: August 7, 1987
    Date of Patent: January 31, 1989
    Assignee: Degussa Aktiengesellschaft
    Inventors: Rainer Siegmeier, Gu Prescher, Helmut Maurer
  • Patent number: 4772727
    Abstract: 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: Grant
    Filed: August 7, 1987
    Date of Patent: September 20, 1988
    Assignee: Degussa
    Inventors: Ian O. Sutherland, Philip C. B. Page, Christopher M. Rayner
  • Patent number: 4760200
    Abstract: 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: Grant
    Filed: December 31, 1985
    Date of Patent: July 26, 1988
    Assignee: Union Carbide Corporation
    Inventors: Brian T. Keen, John H. Robson, George E. Keller, II
  • Patent number: 4701571
    Abstract: 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: Grant
    Filed: June 30, 1986
    Date of Patent: October 20, 1987
    Assignee: Union Carbide Corporation
    Inventors: Hwaili Soo, John H. Robson
  • Patent number: 4661646
    Abstract: 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: Grant
    Filed: November 21, 1985
    Date of Patent: April 28, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf Schalenbach, Helmut Waldmann
  • Patent number: 4644085
    Abstract: 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: Grant
    Filed: June 4, 1985
    Date of Patent: February 17, 1987
    Assignee: Rooperol (NA) NV
    Inventors: Siegfried Drewes, Roelof W. Liebenberg
  • Patent number: 4626603
    Abstract: 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: Grant
    Filed: November 15, 1985
    Date of Patent: December 2, 1986
    Assignee: Degussa Aktiengesellschaft
    Inventors: Rainer Siegmeier, Gunter Prescher, Helmut Maurer
  • Patent number: 4626604
    Abstract: 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: Grant
    Filed: September 11, 1985
    Date of Patent: December 2, 1986
    Assignee: Davy McKee (London) Limited
    Inventors: Andrew G. Hiles, John E. Logsdon
  • Patent number: 4579982
    Abstract: 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: Grant
    Filed: March 28, 1984
    Date of Patent: April 1, 1986
    Assignee: Union Carbide Corporation
    Inventors: John R. Briggs, John H. Robson
  • Patent number: 4579983
    Abstract: 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: Grant
    Filed: March 28, 1984
    Date of Patent: April 1, 1986
    Assignee: Union Carbide Corporation
    Inventor: Brian T. Keen
  • Patent number: 4578524
    Abstract: 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: Grant
    Filed: March 28, 1984
    Date of Patent: March 25, 1986
    Assignee: Union Carbide Corporation
    Inventor: Brian T. Keen
  • Patent number: 4571440
    Abstract: 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: Grant
    Filed: October 23, 1984
    Date of Patent: February 18, 1986
    Assignee: Union Carbide Corporation
    Inventors: Brian T. Keen, John H. Robson
  • Patent number: 4564715
    Abstract: 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: Grant
    Filed: October 23, 1984
    Date of Patent: January 14, 1986
    Assignee: Union Carbide Corporation
    Inventors: John R. Briggs, George L. O'Connor, John H. Robson
  • Patent number: 4560813
    Abstract: 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: Grant
    Filed: March 28, 1984
    Date of Patent: December 24, 1985
    Assignee: Union Carbide Corporation
    Inventor: Joseph A. Collier
  • Patent number: 4551566
    Abstract: 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: Grant
    Filed: September 8, 1983
    Date of Patent: November 5, 1985
    Assignee: Union Carbide Corporation
    Inventors: John H. Robson, George E. Keller, II
  • Patent number: 4536347
    Abstract: 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: Grant
    Filed: March 19, 1984
    Date of Patent: August 20, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Horner, Matthias Irgang
  • Patent number: 4500463
    Abstract: 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: Grant
    Filed: May 1, 1981
    Date of Patent: February 19, 1985
    Assignees: Eisai Co., Ltd., Agency of Industrial Science & Technology
    Inventors: Akio Sato, Kenji Nakajima, Yoshimasa Takahara, Shizumasa Kijima, Yuichi Inai, Yoshiyuki Kohara, Yoshiyuki Kawakami, Tomio Tsurugi
  • Patent number: 4480123
    Abstract: 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: Grant
    Filed: July 25, 1983
    Date of Patent: October 30, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Hans-Martin Weitz
  • Patent number: 4436940
    Abstract: 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: Grant
    Filed: April 21, 1981
    Date of Patent: March 13, 1984
    Assignee: Standard Oil Company (Indiana)
    Inventors: Ellis K. Fields, William C. Clarke
  • Patent number: 4429139
    Abstract: 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: Grant
    Filed: October 19, 1982
    Date of Patent: January 31, 1984
    Assignee: Firmenich SA
    Inventor: Charles Fehr