Nonring Moiety Becomes Ring Patents (Class 585/358)
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Patent number: 8993819Abstract: The present invention provides a process for preparing cycloheptene and derivatives thereof by ring-closing metathesis of unsymmetric 1,8-dienes whose C—C double bond at the 8 position is nonterminal. Cycloheptene and the cycloheptanone, cycloheptylamine, cycloheptanecarbaldehyde, cycloheptanecarboxylic acid and cycloheptanecarbonyl chloride conversion products thereof, and the derivatives thereof, are important synthesis units for active ingredient compounds. The ring-closing metathesis is preferably performed as a reactive distillation. The unsymmetric 1,8-dienes for the ring-closing metathesis can be obtained by catalytic decarbonylation or oxidative decarboxylation from the corresponding unsaturated carboxylic acids or carboxylic acid derivatives.Type: GrantFiled: July 10, 2012Date of Patent: March 31, 2015Assignee: BASF SEInventors: Joaquim Henrique Teles, Michael Limbach, Richard Dehn, Stephan Deuerlein, Manuel Danz
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Publication number: 20150080623Abstract: A catalytic process is provided which produces in a single reaction branched, cyclic and aromatic hydrocarbons, or cracked straight-chain hydrocarbons, from fatty acids in which the fatty acids are reacted over a multifunctional catalyst and undergo both decarboxylation and a further transformation (isomerization, cyclization, aromatization, or cracking) to form reaction products useful as fuels and for other applications that require a source of energy, or as feedstock for hydrocarbon-based commercial products such as surfactants, solvents and lubricants.Type: ApplicationFiled: September 18, 2014Publication date: March 19, 2015Inventors: Paul Ratnasamy, Moises A. Carron, Masoudeh Ahmadi
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Publication number: 20140163268Abstract: A process for converting triacylglycerides-containing oils into crude oil precursors and/or distillate hydrocarbon fuels is disclosed. The process may include reacting a triacylglycerides-containing oil-carbon dioxide mixture at a temperature in the range from about 250° C. to about 525° C. and a pressure greater than about 75 bar to convert at least a portion of the triacylglycerides to a hydrocarbon or mixture of hydrocarbons comprising one or more of isoolefins, isoparaffins, cycloolefins, cycloparaffins, and aromatics.Type: ApplicationFiled: December 11, 2012Publication date: June 12, 2014Applicant: LUMMUS TECHNOLOGY INC.Inventor: Marvin I. Greene
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Patent number: 8450545Abstract: A process of modifying a zeolite catalyst to produce a modified zeolite catalyst wherein the modified zeolite catalyst has blocked pore sites. An oxygenated feed is flowed over the modified zeolite catalyst, wherein the oxygenated feed comprises hydrocarbons, methanol and dimethyl ether or a mixture thereof. The hydrocarbons, methanol and dimethyl ether in the oxygenated feed react with the modified zeolite catalyst to produce cyclic hydrocarbons, wherein the cyclic hydrocarbons produced has less than 10% durene and a median carbon number is C8.Type: GrantFiled: July 24, 2009Date of Patent: May 28, 2013Assignee: Phillips 66 CompanyInventors: Glenn W. Dodwell, Joe D. Allison, Shetian Liu, Scott McQueen, Dennis G. Schultz, Byron G. Johnson, Madhu Anand, Melinda L. Johnson, Larry E. Reed, Brian C. Dunn
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Publication number: 20130018213Abstract: Embodiments of methods for making renewable diesel by deoxygenating (decarboxylating/decarbonylating/dehydrating) fatty acids to produce hydrocarbons are disclosed. Fatty acids are exposed to a catalyst selected from a) Pt and MO3 on ZrO2 (M is W, Mo, or a combination thereof), or b) Pt/Ge or Pt/Sn on carbon, and the catalyst decarboxylates at least 10% of the fatty acids. In particular embodiments, the catalyst consists essentially of 0.7 wt % Pt and 12 wt % WO3, relative to a mass of catalyst, or the catalyst consists essentially of a) 5 wt % Pt and b) 0.5 wt % Ge or 0.5 wt % Sn, relative to a mass of catalyst. Deoxygenation is performed without added hydrogen and at less than 100 psi. Disclosed embodiments of the catalysts deoxygenate at least 10% of fatty acids in a fatty acid feed, and remain capable of deoxygenating fatty acids for at least 200 minutes to more than 350 hours.Type: ApplicationFiled: September 14, 2012Publication date: January 17, 2013Inventors: Richard T. Hallen, Karl O. Albrecht, Heather M. Brown, James F. White
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Publication number: 20130018205Abstract: The present invention provides a process for preparing cycloheptene and derivatives thereof by ring-closing metathesis of unsymmetric 1,8-dienes whose C—C double bond at the 8 position is nonterminal. Cycloheptene and the cycloheptanone, cycloheptylamine, cycloheptanecarbaldehyde, cycloheptanecarboxylic acid and cycloheptanecarbonyl chloride conversion products thereof, and the derivatives thereof, are important synthesis units for active ingredient compounds. The ring-closing metathesis is preferably performed as a reactive distillation. The unsymmetric 1,8-dienes for the ring-closing metathesis can be obtained by catalytic decarbonylation or oxidative decarboxylation from the corresponding unsaturated carboxylic acids or carboxylic acid derivatives.Type: ApplicationFiled: July 10, 2012Publication date: January 17, 2013Applicant: BASF SEInventors: Joaquim Henrique TELES, Michael Limbach, Richard Dehn, Stephan Deuerlein, Manuel Danz
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Publication number: 20110245542Abstract: Processes and reactor systems are provided for the conversion of oxygenated hydrocarbons to hydrocarbons, ketones and alcohols useful as liquid fuels, such as gasoline, jet fuel or diesel fuel, and industrial chemicals. The process involves the conversion of mono-oxygenated hydrocarbons, such as alcohols, ketones, aldehydes, furans, carboxylic acids, diols, triols, and/or other polyols, to C4+ hydrocarbons, alcohols and/or ketones, by condensation. The oxygenated hydrocarbons may originate from any source, but are preferably derived from biomass.Type: ApplicationFiled: June 17, 2011Publication date: October 6, 2011Applicant: Virent Energy Systems, Inc.Inventors: Randy D. Cortright, Paul G. Blommel
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Publication number: 20070265184Abstract: Preparation of cyclododecatriene in a continuous or discontinuous process by trimerization of butadiene in the presence of a catalyst system and a solvent, the crude cyclododecatriene obtained being able to be isolated by means of distillation. The cyclooctadiene formed as by-product can likewise be isolated from the crude product.Type: ApplicationFiled: March 20, 2007Publication date: November 15, 2007Applicant: DEGUSSA AGInventors: Jurgen Herwig, Wilhelm Brugging, Martin Roos, Norbert Wilczok
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Patent number: 7151199Abstract: Hydrocarbon or oxygenate conversion process in which a feedstock is contacted with a non zeolitic molecular sieve which has been treated to remove most, if not all, of the halogen contained in the catalyst. The halogen may be removed by one of several methods. One method includes heating the catalyst in a low moisture environment, followed by contacting the heated catalyst with air and/or steam. Another method includes steam-treating the catalyst at a temperature from 400° C. to 1000° C. The hydrocarbon or oxygenate conversion processes include the conversion of oxygenates to olefins, the conversion of oxygenates and ammonia to alkylamines, the conversion of oxygenates and aromatic compounds to alkylated aromatic compounds, cracking and dewaxing.Type: GrantFiled: June 10, 2002Date of Patent: December 19, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Luc Roger Marc Martens, Stephen N. Vaughn, Albert Edward Schweizer, John K. Pierce, Shun Chong Fung
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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: 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: 6028237Abstract: The present invention relates generally to novel methods for the synthesis of cyclopropylacetylene which is a reagent in the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one which is a useful human immunodeficiency virus (HIV) reverse transcriptase inhibitor.Type: GrantFiled: December 15, 1997Date of Patent: February 22, 2000Assignee: DuPont Pharmaceuticals CompanyInventor: Rodney Lawrence Parsons, Jr.
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Patent number: 5952537Abstract: The process of invention reacts an alkynyl halide with a mixture that includes a dialkylaminomagnesium halide or a bis(dialkylamino)magnesium compound to produce a cycloalkylacetylene compound. Preferably, the dialkylaminomagnesium halide compound is of the general formula R.sub.2 NMgX (where R is a linear, branched, or cyclic alkyl substituent or R.sub.2 N represents a heterocyclic alkyl amine and X is Cl, Br, or I) and the bis(dialkylamino)magnesium compound is of the general formula (R.sub.2 N).sub.2 Mg (where R is a linear, branched, or cyclic alkyl substituent or R.sub.2 N represents a heterocyclic alkylamine). In a preferred method of the invention, the reaction is conducted at moderate temperatures for a period of about 12 to 24 hours. The reaction mixture preferably includes tetrahydrofuran (THF), or a hydrocarbon, or a hydrocarbonether mixture.Type: GrantFiled: March 13, 1998Date of Patent: September 14, 1999Assignee: Wiley Organics, Inc.Inventors: Kurt R. Stickley, David B. Wiley
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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: 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: 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: 5194619Abstract: The compounds of the formula I or Ia ##STR1## in which R.sup.1 is alkyl, aryl, alkoxy, alkenyl, arylalkyl, alkylaryl, aryloxy, fluoroalkyl, halogenoaryl, alkynyl, trialkylsilyl or a heteroaromatic radical,R.sup.2, R.sup.3 and R.sup.4, in addition to hydrogen, have the meanings given under R.sup.1 andR.sup.5 is hydrogen, alkyl, fluoroalkyl or alkenyl, can be obtained in a one-stage process by reaction of a compound II ##STR2## with (substituted) cyclopentadiene in the presence of a base. The compounds I and Ia are suitable as ligands for metallocene complexes which are used as catalysts in olefin polymerization.Type: GrantFiled: February 14, 1992Date of Patent: March 16, 1993Assignee: Hoechst AktiengesellschaftInventors: Dieter Reuschling, Jurgen Rohrmann, Gerhard Erker, Reiner Nolte, Michael Aulbach, Astrid Weiss
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Patent number: 5089469Abstract: Described are isomeric mixtures of bisabolene prepared by dehydrating nerolidol using citric acid or phosphoric acid and then distilling the resulting product at particular temperature ranges and particular pressure ranges in order to prepare a composition of matter useful for augmenting or enhancing natural, dry, floral, opoponax aromas with floral, freesia, fruity, citrus, bergamot, mango and opoponax topnotes in perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic, or zwitterionic detergents, fabric softener compositions, drier-added fabric softener articles, cosmetic powders and the like; and useful for repelling specific species of insects, namely, house flies Musca domestica L. (Diptera Muscidae)) and the species of mosquitoes, Aedes aegypti.Type: GrantFiled: April 25, 1991Date of Patent: February 18, 1992Assignee: International Flavors & Fragrances Inc.Inventors: Michael J. Zampino, Richard A. Wilson, Braja D. Mookherjee
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Patent number: 4967033Abstract: The polyunsaturated compounds of formula ##STR1## having two conjugated double bonds in the endo- and exo- positions of the pentagonal cycle indicated by the dotted lines, and wherein symbols R.sup.1 and R.sup.2, when taken separately, represent respectively a. a linear or brached C.sub.1 to C.sub.4 alkyl radical and b. an hydrogen atom or a methyl radical, or, when taken together with the carbon atoms to which they are bonded form a polymethylenic cycle such as indicated by the dotted line, containing from 5 to 12 carbon atoms, and symbol R.sup.3 stands for an hydrogen atom or a methyl radical, n being an integer equal to 0 or 1, which are useful intermediate products for the preparation of odoriferous macrocyclic ketones, are prepared according to a process comprising a vapor phase cyclization of an enone of formula ##STR2## wherein the dotted line and the symbols n, R.sup.1, R.sup.2 and R.sup.Type: GrantFiled: January 31, 1990Date of Patent: October 30, 1990Assignee: Firmenich S.A.Inventor: Cyril Mahaim
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Patent number: 4627911Abstract: A catalytic cracking process is described in which methanol is a coreactant with gas oil in combination with a small amount (catalyst/oil 0.01) of a dispersed, very fine, and highly active catalyst powder, such as ZSM-5B. The methanol is preferably admixed with the catalyst before admixture with the oil in order to protect the catalyst from adsorption of poisonous compounds (e.g., nitrogenous compounds) during the initial stages of the reaction, particularly if the methanol is insoluble in a non-polar hydrocarbon feed. The premixed materials are fed into a riser reactor. The residence time in the reactor is 6-15 seconds. Preferably, the catalyst is not regenerated. The quantity of methanol is maintained so that its exothermic reaction is approximately heat balanced with the endothermic catalytic cracking reaction.Type: GrantFiled: December 30, 1985Date of Patent: December 9, 1986Assignee: Mobil Oil CorporationInventors: Nai Y. Chen, Thomas F. Degnan, Jr.
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Patent number: 4568782Abstract: Disclosed is the vapor phase cyclodehydration of an aldehyde or ketone over a solid Lewis acid as catalyst to make indene or a substituted indene according to the equation: ##STR1##Type: GrantFiled: June 17, 1985Date of Patent: February 4, 1986Assignee: The Standard Oil CompanyInventors: Marco Pagnotta, Mark C. Cesa, James D. Burrington
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Patent number: 4472313Abstract: The invention provides a method of converting ethylenically unsaturated units of an olefinic substrate to corresponding cyclopropanyl units, comprising treating the olefinic substrate, in an ether medium, with zinc and diiodomethane and a catalytic amount of a metallo-hydride reducing agent. Preferred substrates are olefinic fatty acids or their functional derivatives, e.g. oleic acid esters.Type: GrantFiled: September 20, 1982Date of Patent: September 18, 1984Assignee: Sandoz, Inc.Inventors: Urs Giger, Oljan Repic
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Patent number: 4179468Abstract: Acyclic terpenoid onium salts are cyclized in an acidic aqueous solution at a temperature of at least about 80.degree. C.Type: GrantFiled: June 19, 1978Date of Patent: December 18, 1979Assignee: SCM CorporationInventors: Bernard J. Kane, Richard A. Von Genk