From Nonhydrocarbon Patents (Class 585/357)
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Patent number: 6552239Abstract: The present invention relates to a process for the preparation of cyclopropaneacetylene by reacting a ketophosphonate with a diazo-transfer reagent in the presence of non-nucleophilic base in an aprotic solvent to generate a reaction mixture containing a ketodiazophosphonate compound and then reacting the reaction mixture with cyclopropanecarboxaldehyde in a non-nucleophilic base and a protic solvent to yield cyclopropaneacetylene.Type: GrantFiled: October 27, 2000Date of Patent: April 22, 2003Assignee: Merck & Co., Inc.Inventor: Karel M. J. Brands
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Patent number: 6462206Abstract: Ketones and aldehydes are hydrogenated to the corresponding alcohol or alkyl group, using H2 gas as the stoichiometric reductant, and organometallic ruthenium complexes as the catalysts.Type: GrantFiled: June 20, 2001Date of Patent: October 8, 2002Assignees: E. I. du Pont de Nemours and Company, Brookhaven Science AssociatesInventors: R. Morris Bullock, Marcel Schlaf, Elisabeth M. Hauptman
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Patent number: 6417405Abstract: Substituted or unsubstituted cyclopentadienyl are prepared by reducing 4-ketocyclopentene to an alcohol, replacing the hydroxyl functionality with a leaving group and deprotonating the resulting product under base induced elimination conditions.Type: GrantFiled: June 20, 2001Date of Patent: July 9, 2002Assignee: The Dow Chemical CompanyInventor: Ravi B. Shankar
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Patent number: 6388151Abstract: A method for synthesizing tetramethylcyclopentadiene from 2,3-dibromobutane is described. A 2-bromo-2-butene Grignard is reacted with an ethyl formate to produce a 3,5-dimethyl-2,5-heptadiene-4-ol magnesium bromide which is then quenched with acetic acid to produce 3,5-dimethyl-2,5-hepadiene-4-ol.Type: GrantFiled: November 24, 1998Date of Patent: May 14, 2002Assignee: Boulder Scientific CompanyInventors: Jeffrey M. Sullivan, Richard D. Crawford
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Publication number: 20010051756Abstract: The present invention relates to a method to prepare cyclopropenes.Type: ApplicationFiled: April 4, 2001Publication date: December 13, 2001Inventor: Richard Martin Jacobson
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Patent number: 6288297Abstract: The present invention relates generally to novel methods for the synthesis of cyclopropylacetylene which is an essential reagent in the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one; a useful human immunodeficiency virus (HIV) reverse transcriptase inhibitor. In the process, for example, cyclopropane carboxaldehyde is alkylated to form 1,1,1-trichloro-2-cyclopropyl-ethanol; which in turn is hydroxy protected to form 1,1,1-trichloro-2-cyclopropylethyltosylate; which in turn undergoes elimination to form cyclopropyl acetylene. This improvement provides for high conversion of inexpensive, readily available starting materials into cyclopropylacetylene, high overall yields and can be conducted on an industrial scale.Type: GrantFiled: September 30, 1999Date of Patent: September 11, 2001Assignee: Dupont Pharmaceuticals CompanyInventors: Zhe Wang, Jianguo Yin, Joseph M. Fortunak, Silvio Campagna
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Publication number: 20010012902Abstract: A process for producing a crosslink-cyclized cyclopentadiene, comprising the steps of reacting a cyclopentenone with an alkali metal hydride to thereby reduce the cyclopentenone (reduction step A) into a cyclopentenol; and reacting the cyclopentenol with a dehydrating agent to thereby dehydrate the cyclopentenol (dehydration step B) into a crosslink-cyclized cyclopentadiene of the general formula (III): 1Type: ApplicationFiled: January 31, 2001Publication date: August 9, 2001Inventor: Keiichi Yokoyama
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Patent number: 6002062Abstract: Ethynylcyclopropane is prepared from (1,1-dimethoxyethyl)cyclopropane by a two-stage elimination of methanol. Ethynylcyclopropane is an intermediate in the synthesis of pharmaceutically active ingredients, for example, antiviral agents.Type: GrantFiled: December 4, 1998Date of Patent: December 14, 1999Assignee: Lonza AGInventors: Dominique Michel, Paul Hanselmann
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Patent number: 5977421Abstract: The amount of limonene produced during pyrolysis of scrap tire carcass or polyisoprene rubber can be increased by decreasing residence time of the isoprene gas produced during the thermal degradation of polyisoprene rubber in the high temperature reactor region of an oven. This is achieved by using a novel oven design which permits rapid expansion of the isoprene gas away from the high temperature reactor region of the oven to a cooler region where the gas forms limonene and condenses. This pyrolysis method also decreases the amount of soot produced while increasing the amount of limonene produced. Furthermore, this system readily enables separation of the solid, liquid and gas phases produced during pyrolysis.Type: GrantFiled: September 3, 1997Date of Patent: November 2, 1999Inventors: Curtiss D. Hanson, Timothy Burrell, James E. Haworth, James A. Olson
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Patent number: 5936134Abstract: A method for producing synthetical oils and storable products of calorific energy, by co-processing waste rubber materials, especially waste tires, and coal optionally in the presence of a material containing Fe as a catalyst, comprising the steps of mixing triturated waste rubber material having a particle size of preferredly 1-5 mm, and coal having particle sizes of 0.2-1 mm, and, when used, the catalyst having a referred particle size of 0.05-0.015 mm, until obtaining a mixture, heating the mixture in a reactor to a temperature between 300.degree. C. and 500.degree. C., during 3-180 minutes, at a pressure between atmospheric pressure and 10 MPa, to enable a processing step basically consisting of a pyrolysis/hydropyrolysis. During the processing step, there is a generation of gases containing approximately 50% CO and CO.sub.2, and approximately another 50% by volume of C.sub.1 -C.sub.4 hydrocarbons, and having a calorific energy between 6000 and 8000 kcal/Nm.sup.Type: GrantFiled: March 26, 1997Date of Patent: August 10, 1999Assignee: Consejo Superior Investigaciones CientificasInventors: Ana Maria Mastral Lamarca, Ramon Murillo Villuendas
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Patent number: 5900517Abstract: Cyclopentadienyl derivatives are described having general formula (I) ##STR1## where R, R.sub.1, R.sub.2, R.sub.4, equivalent to or different from one another, are selected from: --H, alkyl radicals having a number of carbon atoms from 1 to 5, cycloalkyl radicals having a number of carbon atoms from 5 to 8, aryl and alkylaryl radicals having a number of carbon atoms from 6 to 8, aralkyl radicals having a number of carbon atoms from 7 to 9; n is an integer from 2 to 18; with the proviso that the number of R different from H does not exceed 2; with the exclusion of the compound having n=3, R.dbd.R.sub.1 .dbd.R.sub.2 .dbd.R.sub.4 .dbd.H. The invention a-so describes the process for the preparation of the above-mentioned cyclopentadienyl derivatives.Type: GrantFiled: August 12, 1996Date of Patent: May 4, 1999Assignee: Enichem S.p.A.Inventors: Paolo Biagini, Roberto Santi, Giampiero Borsotti, Gabriele Lugli, Viviano Banzi
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Patent number: 5723708Abstract: A method for producing cyclopentadienes which comprises the step of cyclodehydration of an unsaturated carbonyl compound having a specific chemical structure in a vapor phase in the presence of a specific solid acid catalyst. The cyclopentadienes of the invention can be produced in a high yield from inexpensive starting materials through a simplified reaction process and are useful as intermediate compounds for organic synthesis.Type: GrantFiled: September 27, 1995Date of Patent: March 3, 1998Assignee: Nippon Petrochemicals Company, LimitedInventors: Yasuo Matsumura, Kazuharu Suyama, Yoshihisa Inomata
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Patent number: 5710299Abstract: Bridged metallocene compounds are produced by a process of promising commercial utility for plant-sized operations. The overall process involves the direct conversion of benzoindanones to benzoindanols which, without isolation, are converted to benzoindenes. Thereupon the benzoindenes are bridged by deprotonating the benzoindenes with a strong base such as butyllithium and reacting the resultant deprotonated product with a suitable silicon-, germanium- or tin-containing bridging reactant such as dichlorodimethylsilane. The resultant bridged product is deprotonated with a strong base such as butyllithium and reacted with a suitable Group IV, V, or VI metal-containing reactant such as ZrCl.sub.4 to provide a silicon-, germanium- or tin-bridged Group IV, V, or VI metal complex, such as a dihydrocarbylsilyl-bridged zirconocene complex.Type: GrantFiled: June 27, 1996Date of Patent: January 20, 1998Assignee: Albemarle CorporationInventors: Meng-Sheng Ao, Hassan Y. Elnagar, Arcelio J. Malcolm, Jamie R. Strickler
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Patent number: 5648578Abstract: A process for preparing tetraalkylated cyclopentadienes comprises (a) pyrolyzing an isobornyl carboxylate so as to form a mixture of 1,2,3- and 1,2,4-trimethylcyclopentadienes, (b) alkylating said mixture with an alkylating agent so as to form a mixture of alkyltrimethylcyclopentadiene isomers including 1,2,3,4-alkyltrimethylcyclopentadiene and, (c) thermally isomerizing the mixture of isomers obtained in step (b) so as to increase the proportion of 1,2,3,4-alkyltrimethylcyclopentadiene in said mixture of isomers.Type: GrantFiled: April 26, 1995Date of Patent: July 15, 1997Assignee: Albemarle CorporationInventors: William J. Layman, Gene C. Robinson
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Patent number: 5600047Abstract: A process for producing an optically active olefin represented by a formula ##STR1## wherein R.sup.1 represents an organic group and X represents a polycyclic carbon ring group, by reacting a corresponding optically active ester derivative represented by a formula ##STR2## wherein R.sup.1 and X are as defined above and R represents a hydrogen atom, an alkoxy group, an alkenyloxy group or a substituted or unsubstituted aralkyloxy group, with formic acid or a salt thereof in the presence of a catalyst comprising a palladium salt and a tertiary phosphine.Said process makes it possible to produce, at a high yield at a high selectivity, an optically active olefin which has a physiological activity and is useful as a medicine or is useful as an intermediate for the synthesis of physiologically active steroids. Further, said process uses no harmful reagent such as mercury or the like. Thus, it is advantageous as an industrial process.Type: GrantFiled: June 2, 1995Date of Patent: February 4, 1997Assignee: Kuraray Co., Ltd.Inventors: Tadakatsu Mandai, Jiro Tsuji, Manzo Shiono
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Patent number: 5434324Abstract: Alkyl substituted cyclopentadienes are prepared by reacting cyclopentenones with a Grignard reagent followed by the acidification and dehydration of the resulting tertiary alcohol with an organic carboxylic acid.Type: GrantFiled: October 15, 1993Date of Patent: July 18, 1995Assignee: Albemarle CorporationInventors: John Y. Lee, Meng-Sheng Ao
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Patent number: 5414173Abstract: A process of preparing cyclopentadiene or substituted cyclopentadienes, such as tetramethylcyclopentadiene. The process involves contacting under reaction conditions cyclopentenol or a substituted cyclopentenol with a catalyst selected from (1) crystalline and amorphous aluminum phosphates, (2) aluminophosphate molecular sieves, and (3) silicoaluminophosphate molecular sieves. The process produces cyclopentadienes in high isolated yields.Type: GrantFiled: December 22, 1993Date of Patent: May 9, 1995Assignee: The Dow Chemical CompanyInventors: Juan M. Garces, Guo-shuh J. Lee, David R. Wilson
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Patent number: 5329056Abstract: A process is provided for preparing an substituted cyclopentadiene by the steps of (a) reacting a vinyl ketone with a vinyl organometallic compound to form a divinyl tertiary alcohol and (b) dehydrating/cyclizing the tertiary alcohol such as with an acid and/or heat to form the substituted cyclopentadiene.Type: GrantFiled: January 19, 1993Date of Patent: July 12, 1994Assignee: Albemarle CorporationInventor: Stephen E. Belmont
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Patent number: 5082953Abstract: A sulpholene compound and more particularly 4,4-dimethyl-2,2-dioxo-1,2,4,5,6,7-hexahydro-benzo[c]thiophene. These compounds are prepared by bringing myrcene sulphone into contact with a strong acid. The compounds of the present invention can be used as synthesis intermediates in the preparation of vitamin A.Type: GrantFiled: March 4, 1991Date of Patent: January 21, 1992Assignee: Rhone Poulenc Nutrition AnimaleInventor: Jean-Pierre Duchesne
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Patent number: 4935567Abstract: A cellulose-containing biomass such as wood is liquefied by heat-treatment under a pressurized condition in the presence of water and a neutral, oxygen-containing organic liquid such as an ester, ether, ketone or alcohol. An alkaline catalyst such as potassium carbonate may be added to accelerate the liquefaction when the organic liquid is one other than acetone. Also provided is a process for the liquefaction of a cellulose-containing biomass including heat-treating the biomass in an aqueous medium in the pressurized atmosphere of an inert gas or steam at a temperature of 250.degree.-385.degree. C. in the presence of an alkaline catalyst in an amount of 0.01-0.1 part by weight per one part by weight of the biomass on the dry basis.Type: GrantFiled: June 6, 1986Date of Patent: June 19, 1990Assignee: Agency of Industrial Science and TechnologyInventors: Shinya Yokoyama, Tomoko Ogi, Katsuya Koguchi
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Patent number: 4895996Abstract: Alkenes are prepared by the hydroboration of enamines followed by an elimination reaction to form the alkene. This process has wide applicability and is useful for the stereospecific synthesis of [Z] isomers. It is preferred to use 9-borabicyclo[3.3.1 nonane as the hydroborating agent and to use methanol to catalyze the elimination reaction.Type: GrantFiled: October 17, 1988Date of Patent: January 23, 1990Assignees: Purdue Research Foundation, The Dow Chemical CompanyInventors: Christian T. Goralski, Bakthan Singaram, Herbert C. Brown
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Patent number: 4886924Abstract: A process for the stereospecific synthesis of [E] alkenes from enamines comprising the steps of hydroborating the enamine; esterifying the organoborane so formed and oxidizing the boronic ester in the presence of hydrogen peroxide and in the absence of added base under conditions sufficient to form the [E] alkene in high yield.Type: GrantFiled: October 17, 1988Date of Patent: December 12, 1989Assignee: The Dow Chemical CompanyInventors: Christian T. Goralski, Bakthan Singaram, Herbert C. Brown
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Patent number: 4849574Abstract: Ketones or aldehydes are methylenated to form the corresponding olefin by reaction with a bis(alkylchloroalumino)methane, e.g., in the form of its dietherate.Type: GrantFiled: September 2, 1988Date of Patent: July 18, 1989Assignee: Texas Alkyls, Inc.Inventors: Andrzej M. Piotrowski, Dennis B. Malpass
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Patent number: 4847425Abstract: 4-isopropylcyclohexylmethanol and its alkyl ethers of the general formula I ##STR1## where R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl, are prepared by a process in which the novel 4-(1-alkoxy-1-methylethyl)-benzaldehyde or its dialkyl acetal of the general formula II ##STR2## where X is oxygen (IIa) or its two R.sup.2 O groups (IIb) and R.sup.2 and R.sup.3 are each C.sub.1 -C.sub.4 -alkyl, is heated to 100.degree.-250.degree. C., preferably 130.degree.-200.degree. C., under a hydrogen pressure of from 50 to 350, preferably from 150 to 300, bar in the presence of a noble metal of group VIII of the Periodic Table.Type: GrantFiled: May 31, 1988Date of Patent: July 11, 1989Assignee: BASF AktiengesellschaftInventors: Dieter Degner, Walter Gramlich, Wolfgang Lengsfeld, Ludwig Schuster
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Patent number: 4814532Abstract: A process for producing an alkylcyclopentadiene derivative comprising the vapor-phase reaction of a cyclopentadiene derivative and an aliphatic lower alcohol in the presence of a basic crystalline aluminosilicate catalyst containing an alkali metal.Type: GrantFiled: May 22, 1987Date of Patent: March 21, 1989Assignees: Chemical Company, Ltd. Asahi, Zenichi YoshidaInventors: Zenichi Yoshida, Susumu Kato, Yashuhiro Amemiya
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Patent number: 4788367Abstract: Ketones are methylenated to form the corresponding olefin by reaction with a bis(alkylchloroalumino)methane, e.g., in the form of its dietherate.Type: GrantFiled: November 5, 1987Date of Patent: November 29, 1988Assignee: Texas Alkyls Inc.Inventors: Andrzej M. Piotrowski, Dennis B. Malpass
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Patent number: 4788368Abstract: Ketones are alkylenated to form the corresponding olefin by reaction with a bis(substituted alumino)substituted methane, e.g., in the form of its dietherate.Type: GrantFiled: November 5, 1987Date of Patent: November 29, 1988Assignee: Texas Alkyls Inc.Inventors: Andrzej M. Piotrowski, Dennis B. Malpass, John J. Eisch, Marek P. Boleslawski
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Patent number: 4751307Abstract: Disclosed are improved Wittig reaction processes wherein the Wittig reaction is conducted in an anisole containing solvent.Type: GrantFiled: February 27, 1987Date of Patent: June 14, 1988Assignee: Mallinckrodt, Inc.Inventor: Carl R. White
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Patent number: 4728672Abstract: A process for producing hydrocarbons which comprises bringing a gas mixture comprising hydrogen and carbon monoxide into contact with a catalyst comprising manganese oxide, alkali metal, sulfur, and ruthenium to produce hydrocarbons. The hydrocarbons formed are rich in olefins. When a catalyst prepared by combining the above described catalyst with crystalline zeolite is used, the hydrocarbons formed becomes rich in liquid hydrocarbons, particularly, a gasoline fraction.Type: GrantFiled: December 11, 1986Date of Patent: March 1, 1988Assignee: Research Association for Petroleum Alternatives DevelopmentInventors: Tomohiro Yoshinari, Fujio Suganuma, Chikara Sera
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Patent number: 4636537Abstract: Polymeric cyclopentadiene derivatives, method for preparing polymeric cyclopentadiene derivatives, and use of polymeric cyclopentadiene derivatives in curable binder compositions.Type: GrantFiled: April 12, 1985Date of Patent: January 13, 1987Assignee: Ashland Oil, Inc.Inventors: Bruce A. Gruber, Heimo J. Langer, William R. Dunnayant
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Patent number: 4604480Abstract: A method for the preparation of a first sulfone compound of the formula: ##STR1## wherein R.sub.a is ##STR2## where R.sub.b is Br and R.sub.c is H except that R.sub.b and R.sub.c together may be an electron pair when R.sub.6 is a radical of the formula: ##STR3## wherein X.sub.1 is independently chlorine, bromine or iodine and R.sub.1 and R.sub.2 are independently at each occurrence hydrogen or, substituted or unsubstituted, phenyl or alkyl where the substituents are halogen or alkoxy or additional --SO.sub.2 Br groups; provided that, each carbon atom of R.sub.1 or R.sub.2 which contains --SO.sub.2 Br also contains an X.sub.1 group and wherein R.sub.3 through R.sub.9 are independently --OZ,--C.sub.6 M.sub.5,--Z,--SiZ.sub.3 or --X.sub.2, where Z is hydrogen or substituted or unsubstituted phenyl, alkyl, alkenyl or alkynyl; X.sub.2 is chlorine, bromine, iodine or fluorine; M is independently at each occurrence Z or X.sub.2 ; R.sub.3 and R.sub.4 may together be an electron pair; two or more of R.sub.3, R.sub.Type: GrantFiled: August 15, 1983Date of Patent: August 5, 1986Assignee: The Research Foundation of State University of New YorkInventors: Eric Block, Mohammad Aslam
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Patent number: 4517171Abstract: Hydrogen and methane are synthesized from a gaseous feed comprising a mixture of H.sub.2 S and CO by contacting said feed with a catalyst comprising a sulfided rutile titania at a temperature of at least about 275.degree. C.Type: GrantFiled: June 29, 1984Date of Patent: May 14, 1985Assignee: Exxon Research and Engineering Co.Inventors: Charles T. Ratcliffe, Petrus J. Tromp
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Patent number: 4499314Abstract: A process for producing hydrocarbons comprising contacting, under conversion conditions, an aqueous methanol with a crystalline aluminosilicate zeolite catalyst which is hydrothermally stable in the temperature range of from 250.degree. C. to 500.degree. C. and is capable of converting methanol to hydrocarbons, and with a promoter comprising one or more compounds selected from the group consisting of aromatic hydrocarbons, precursors to aromatic hydrocarbons, olefins, precursors to olefins and aldehydes to form a mixture comprising light olefins, lower alkanes and monocyclic aromatic hydrocarbons and recovering said hydrocarbons.Type: GrantFiled: April 30, 1984Date of Patent: February 12, 1985Assignee: Imperial Chemical Industries PLCInventors: Duncan Seddon, Thomas Mole, Judy A. Whiteside
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Patent number: 4463194Abstract: A process for making piperitone from crude plinols involving hydrogenating the crude plinols to form dihydroplinols and dehydrating the dihydroplinols to yield an iridene. The iridene is then oxidatively cleaved at the unsaturation to form an acyclic dione. The dione is cyclized in the presence of a base to form piperitone.Type: GrantFiled: November 29, 1982Date of Patent: July 31, 1984Assignee: SCM CorporationInventor: Tse-Lok Ho
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Patent number: 4443632Abstract: Compounds of formula ##STR1## having a double bond in one of the positions indicated by the dotted lines and wherein R represents a hydrogen atom or a methyl radical are utilized as starting materials for the preparation of bicyclic unsaturated hydrocarbons of formula ##STR2## (R=H, CH.sub.3). Conversion of (II) to (I) occurs via thermal treatment in the presence of a metal catalyst.Disclosed is also a process for the preparation of (II).Type: GrantFiled: June 22, 1982Date of Patent: April 17, 1984Assignee: Firmenich SAInventors: Karl H. Schulte-Elte, Bernard L. Muller, Eric Maillefer
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Patent number: 4436943Abstract: 2,2-Dicyclohexenylpropane is prepared by heating 4,4'-dioxydicyclohexylpropane in the presence of a strong acid, under pressures from 1 to 50 mbar and at 120.degree. to 220.degree. C., distilling off the 2,2-dicyclohexenylpropane produced with the water formed and separating the water out of the top product from the distillation.Type: GrantFiled: March 21, 1983Date of Patent: March 13, 1984Assignee: Bayer AktiengesellschaftInventors: Gebhard Rauleder, Helmut Waldmann
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Patent number: 4433188Abstract: A process for the preparation of lower olefins from methanol or dimethyl ether by catalytic conversion at from 300.degree. to 550.degree. C. in two stages over borosilicate zeolites, wherein C.sub.2 -C.sub.4 -olefins and C.sub.1 -C.sub.4 -paraffins are removed after the first reaction stage, the C.sub.5.sup.+ hydrocarbons are passed to the second reaction stage, the aromatics are removed from the reaction product of the second stage and the remaining reaction products are recycled. The advantage of this process is an improvement in the yield of olefins.Type: GrantFiled: September 1, 1982Date of Patent: February 21, 1984Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Wolf D. Mross, Matthias Schwarzmann
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Patent number: 4418236Abstract: Gasoline hydrocarbons are produced by a catalytic conversion of methanol under a pressure of about 5 to 100 bars and at temperatures of about 250.degree. to 500.degree. C. The high-hydrocarbon product of the conversion is cooled so as to condense gasoline hydrocarbons. Tail gas is separated and then compressed and recycled to the conversion. In a heating step, liquid methanol is injected into a mixture of tail gas and methanol vapor and the liquid methanol is entirely evaporated. The resulting mixture of tail gas and methanol vapor is heated by about 10.degree. to 40.degree. C. by an indirect heat exchange with the high-hydrocarbon product. The heating step consists of the injection of liquid methanol and of the heating of the mixture of tail gas and methanol vapor and is repeated at least twice. The mixture at a temperature of about 280.degree. to 360.degree. C. is supplied to the catalytic conversion.Type: GrantFiled: September 21, 1982Date of Patent: November 29, 1983Assignee: Metallgesellschaft AktiengesellschaftInventors: Gerhard Cornelius, Wolfgang Hilsebein, Helmut Ried, Adolf W. Gessner
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Patent number: 4412088Abstract: Cyclopentadiene derivatives, method for preparing cyclopentadiene derivatives, and use of cyclopentadiene derivatives in curable binder compositions.Type: GrantFiled: September 10, 1981Date of Patent: October 25, 1983Assignee: Ashland Oil, Inc.Inventors: Bruce A. Gruber, Diether Koch, Heimo J. Langer, William R. Dunnavant
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Patent number: 4393260Abstract: Cyclohexenyl and alkenyl aromatic compounds, such as cyclohexene and styrene, are prepared by a process comprising contacting a corresponding cyclohexyl or alkyl aromatic carboxylic acid, such as cyclohexyl carboxylic acid or 2-phenyl propionic acid, with a decarboxylation catalyst of the formulaM.sub.a M'.sub.b O.sub.xwherem is copper or a combination of copper and molybdenum, andM' is at least one promoter element, such as a Group IA element.Type: GrantFiled: June 5, 1981Date of Patent: July 12, 1983Assignee: The Standard Oil CompanyInventors: Louis J. Velenyi, Serge R. Dolhyj, Andrew S. Krupa
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Patent number: 4338475Abstract: Apparatus and method of utilization for controlling exothermic reactions such as the conversion of methanol to hydrocarbons are discussed. More particularly, the arrangement of apparatus comprising heat exchange tubes and open end baffle tubes for maintaining the hydraulic diameter within restricted limits during contact between vaporous reactant and a fluid bed of catalyst is discussed.Type: GrantFiled: October 3, 1980Date of Patent: July 6, 1982Assignee: Mobil Oil CorporationInventors: Nicholas D. Pennington, James H. Haddad
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Patent number: 4328383Abstract: New process for preparing unsaturated bicyclic hydrocarbons useful as intermediate compounds in the preparation of macrocyclic ketones.Type: GrantFiled: January 12, 1981Date of Patent: May 4, 1982Assignee: S. A. FirmenichInventors: Albert Eschenmoser, Dorothee Felix
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Patent number: 4327233Abstract: A method is provided for producing a carbocyclic compound by contacting an rganic compound containing a 4-8 membered cyclic sulfide with ozone, in the vapor phase, and recovering a product containing a 3-7 membered carbocyclic ring.Type: GrantFiled: March 26, 1981Date of Patent: April 27, 1982Assignee: The United States of America as represented by the Secretary of CommerceInventors: Richard I. Martinez, John T. Herron
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Patent number: 4319066Abstract: Cyclohexenyl and alkenyl aromatic compounds, such as cyclohexene and styrene, are prepared by a process comprising contacting a corresponding cyclohexyl or alkyl aromatic carboxylic acid, such as cyclohexyl carboxylic acid or 2-phenyl propionic acid, with a decarboxylation catalyst of the formulaM.sub.a M'.sub.b O.sub.xwhereM is copper or a combination of copper and molybdenum, andM' is at least one promoter element, such as a Group IA element.Type: GrantFiled: August 1, 1980Date of Patent: March 9, 1982Assignee: The Standard Oil CompanyInventors: Louis J. Velenyi, Serge R. Dolhyj, Andrew S. Krupa
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Patent number: 4300009Abstract: Living plants and animals synthesize and often accumulate a wide variety of organic materials having a molecular weight greater than 150. These include different chemical types such as natural hydrocarbons including rubbery substances, natural resins, and natural glycerides such as oils and fats. These substances, formed in the anabolic process, are collectively called "anabolites".This invention provides a process for catalytically converting certain anabolites to liquid hydrocarbons useful for the manufacture of fuels such as gasoline and chemicals such as para-xylene. Crystalline aluminosilicate zeolites having an effective pore size of greater than about 5 Angstrom units are useful catalysts.Type: GrantFiled: May 15, 1980Date of Patent: November 10, 1981Assignee: Mobil Oil CorporationInventors: Werner O. Haag, Paul G. Rodewald, Paul B. Weisz
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Patent number: 4292458Abstract: A new crystalline borosilicate comprises a molecular sieve material having the following composition in terms of mole ratios of oxides:0.9.+-.0.2 M.sub.2/n O:B.sub.2 O.sub.3 :YSiO.sub.2 :ZH.sub.2 O,wherein M is at least one cation, n is the valence of the cation, Y is a value within the range of 4 to about 600, and Z is a value within the range of 0 to about 160, and providing a specific X-ray diffraction pattern. The borosilicate is used to catalyze various processes, such as isomerization, disproportionation, alkylation, transalkylation, and conversion of alcohols into gasoline-boiling-range products, olefins, and/or aromatics.Type: GrantFiled: August 29, 1980Date of Patent: September 29, 1981Assignee: Standard Oil Company (Indiana)Inventor: Marvin R. Klotz
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Patent number: 4267111Abstract: This invention concerns processes for preparing .beta.-santalol, .beta.-santalene, dihydro-.beta.-santalol, tetrahydro-.beta.-santalol and related compounds from camphene. The invention further concerns novel compounds useful as intermediates in these processes and as fragrance adjuncts.Type: GrantFiled: June 7, 1979Date of Patent: May 12, 1981Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Philip A. Christenson, Derek H. R. Barton
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Patent number: 4263141Abstract: A process for the catalytic production of gasoline hydrocarbons from synthesis gas comprising carbon oxides and hydrogen is disclosed wherein the synthesis gas is fed initially to a methanol synthesis and thereafter effluent from the methanol synthesis is converted to gasoline hydrocarbons in a gasoline synthesis stage. The invention resides in that the entire effluent from the methanol synthesis stage is fed to the gasoline synthesis stage and at least a portion of the residual gases from the gasoline synthesis stage comprising carbon oxides, hydrogen, methane and minor amounts of C.sub.2 -C.sub.4 hydrocarbons is fed to the methanol synthesis stage together with fresh synthesis gas.Type: GrantFiled: October 15, 1979Date of Patent: April 21, 1981Assignee: Metallgesellschaft AktiengesellschaftInventors: Friedrich Moller, Friedemann Marschner, Emil Supp, Walter Boll, Gerhard Cornelius
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Patent number: 4263443Abstract: Hydrocarbons and esters and/or acids are produced by heating aldehydes in the presence of an alcohol or an alcohol equivalent and in the presence of an iodine or bromine moiety and a rhodium or iridium catalyst.Type: GrantFiled: November 22, 1978Date of Patent: April 21, 1981Assignee: Halcon Research and Development Corp.Inventor: John F. White
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Patent number: 4225734Abstract: A process for the production of symmetrical olefins is provided comprising the reductive coupling of ketones and aldehydes with reactive Ti(II) and/or Ti(O) species.Type: GrantFiled: August 8, 1978Date of Patent: September 30, 1980Assignee: The Regents of the University of CaliforniaInventor: John E. McMurry