Halogen Source Is A Compound Other Than Hydrogen Halide Patents (Class 570/261)
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Patent number: 5910617Abstract: The process according to the invention consists in preparing chlorides of aliphatic or cycloaliphatic hydrocarbons by reacting the corresponding mono- or polyalcohol with phosgene or thionyl chloride in the presence of at least one catalyst chosen from hexasubstituted guanidinium halides and their hydrohalides, optionally grafted via one of their radicals to a silica-based support.The chlorides are quickly obtained with good yields and contain few by-products such as carbonates or chloroformates.Type: GrantFiled: June 18, 1998Date of Patent: June 8, 1999Assignee: Societe Nationale Des Poudres Et ExploisfsInventors: Loic Lecomte, Serge Metge, Denis Souyri
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Patent number: 5880318Abstract: Described is a process for easily preparing an .alpha.-bromo,.omega.-chloroalkane which is high in purity represented by the formula: Br(CH.sub.2).sub.n Cl in which n stands for an integer of 4 to 12. The process comprises reacting in an organic solvent an .alpha.,.omega.-dichloroalkane with an .alpha..omega.-dibromoalkane. As the organic solvent, an aprotic nitrogen-containing or sulfur-containing organic solvent having a dielectric constant at 20.degree. C. of 20 or larger, for example, N,N-dimethylformamide, N,N-dimethylacetamide or N,N-dimethylimidazolidinone is preferred.Type: GrantFiled: August 6, 1997Date of Patent: March 9, 1999Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takehiko Fukumoto, Hiroshi Suzuki, Kinya Ogawa, Kazushi Hirokawa
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Patent number: 5856597Abstract: Gaseous anhydrous hydrogen chloride is introduced into an aqueous solution of zinc chloride under conditions effective to produce a more efficient Lucas reagent than a Lucas reagent made by mixing solid, anhydrous zinc chloride with 38% hydrochloric acid. For example, the reaction rate of such Lucas reagent with levo-menthol is much faster and requires a much shorter reaction period than Lucas reagent formed in the conventional manner from anhydrous, solid zinc chloride and concentrated (38%) hydrochloric acid. Also, the conversion to levo-menthyl chloride was higher when using Lucas reagent formed using gaseous anhydrous hydrogen chloride and aqueous zinc chloride solution. Also, Lucas reagent made in this manner is highly amenable to recycling, and requires only addition thereto of hydrogen chloride to replenish the catalyst for an ensuing run.Type: GrantFiled: April 25, 1997Date of Patent: January 5, 1999Assignee: Albemarle CorporationInventors: K. Pushpananda A. Senaratne, Felix M. Orihuela, Arcelio J. Malcolm
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Patent number: 5760255Abstract: The invention is drawn to a process for the conversion of primary and secondary alcohols into the corresponding fluorine compounds in the presence of an organic solvent, 2-3 equivalents of a strong base and perfluoroalkylsulphonyl fluorides, such as perfluorobutanesulphonyl fluoride or higher homologues.Type: GrantFiled: June 25, 1996Date of Patent: June 2, 1998Assignee: Bayer AGInventors: Helmut Vorbruggen, Barbel Bennua-Skalmowski
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Patent number: 5703248Abstract: The present invention concerns a novel process for the selective trihalogenation of ketones employing organic halogen salts.Type: GrantFiled: May 26, 1995Date of Patent: December 30, 1997Inventors: Jeffrey S. Rommel, James T. Traxler, Richard R. Boettcher
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Patent number: 5637781Abstract: The invention relates to a process for the alcoholysis of carbon tetrachloride which consists in simultaneously sending, on the one hand, carbon tetrachloride and, on the other hand, an alcohol ROH, over a catalytic composition, characterized in that the said catalytic composition comprises an aqueous solution of a metal halide.Type: GrantFiled: June 5, 1995Date of Patent: June 10, 1997Assignee: Elf Atochem S.A.Inventors: Yves Correia, Noel Fino, Philippe Leduc
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Patent number: 5569799Abstract: The purpose of this invention is to describe a new process for the manufacture of monochloroethane and dichloroethanes which can be decomposed into ethylene (C.sub.2 H.sub.4) and chloroethene (C.sub.2 H.sub.3 Cl), respectively, and recovered as products. This new process uses ethane (C.sub.2 H.sub.6) and chlorinated ethenes or methanes as feedstocks. The distribution of the products may be adjusted so that either ethylene or chloroethene is the major product. The new process can also be used to produce propylene from propane, and butylene from butane.Type: GrantFiled: April 27, 1995Date of Patent: October 29, 1996Inventors: Wu-Chi Chen, Harvey R. Chen
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Patent number: 5495034Abstract: A method for the preparation of .alpha.-substituted .omega.-dihydroperluoroalkane derivatives of the general formula H(CF.sub.2 CF.sub.2).sub.n R wherein R=H or COOH, and n=1-10 is characterized by oxidizing .alpha., .alpha., .omega.-trihydroperfluoroalcohols with an oxygen gas or an oxygen-containing gas in the presence of a homogeneous copper catalyst and an alkaline agent in an organic solvent with subsequent isolation of the desired product.Type: GrantFiled: July 15, 1994Date of Patent: February 27, 1996Assignee: Hoechst AktiengesellschaftInventors: Irina P. Skibida, Andrei M. Sakharov, Jury L. Bakhmutov, Vladimir F. Denisenkow, Nina P. Martynova
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Patent number: 5384415Abstract: A process for the preparation of a brominated compound which comprises the step of reacting at least one compound selected from the group consisting of a chloroformate, a chlorosulfite and a chlorophosphite with a brominating agent for a time sufficient to obtain at least one brominated compound. In particular, an alcohol is converted into a chloroformate, chlorosulfite or a chlorophosphite, which is then brominated to obtain the desired product. In another embodiment, a brominating agent is reacted with a reactant selected from the group consisting of thionyl chloride, phosgene and phosphorous oxychloride, followed by contacting the reaction product obtained with an alcohol to be brominated.Type: GrantFiled: May 28, 1993Date of Patent: January 24, 1995Assignee: Rhone-Poulenc ChimieInventors: Jean-Manuel Mas, Pascal Metivier
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Patent number: 5354916Abstract: The invention relates to a process for selectively producing alkyl halides from alkanes, such as methane and ethane at low temperatures and low pressures. Optional hydrolysis to the corresponding alcohols may follow. The process involves adding an alkane and an added halogen source to an aqueous solution in a homogeneous system in the presence of a transition metal halide containing complex, for a time, under conditions and in effective amounts that will permit the formation of alkyl monohalides.Type: GrantFiled: January 24, 1994Date of Patent: October 11, 1994Assignee: Exxon Research and Engineering CompanyInventors: Istvan T. Horvath, John M. Millar, Raymond A. Cook
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Patent number: 5241086Abstract: A process for the preparation of a brominated compound which comprises the step of reacting at least one compound selected from the group consisting of a chloroformate, a chlorosulfite and a chlorophosphite with a brominating agent for a time sufficient to obtain at least one brominated compound. In particular, an alcohol is converted into a chloroformate, chlorosulfite or a chlorophosphite, which is then brominated to obtain the desired product. In another embodiment, a brominating agent is reacted with a reactant selected from the group consisting of thionyl chloride, phosgene and phosphorous oxychloride, followed by contacting the reaction product obtained with an alcohol to be brominated.Type: GrantFiled: December 4, 1992Date of Patent: August 31, 1993Assignee: Rhone-Poulenc ChimieInventors: Jean-Manuel Mas, Pascal Metivier
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Patent number: 5227550Abstract: Carbon tetrachloride, which is a material of low value and may be banned due to the problem of the destructiveness against the stratospheric ozone layer, can be efficiently utilized in the preparation of more useful methyl chloride by a catalytic vapor-phase reaction in a vapor mixture of carbon tetrachloride, methyl alcohol and water. The solid catalyst with which the vapor mixture is contacted at 150.degree. to 250.degree. C. is, for example, a zinc chloride catalyst supported on an active carbon carrier. The conversion of carbon tetrachloride is almost 100% when the contacting time is 10 to 20 seconds.Type: GrantFiled: May 13, 1992Date of Patent: July 13, 1993Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takaaki Shimizu, Taishi Kobayashi, Hironori Iwasaki
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Patent number: 5196611Abstract: The preparation of an alkyl, alkenyl, or alkynyl chloride by the reaction of a corresponding alcohol with phosgene or thionyl chloride in the presence of a phosphine oxide acting as catalyst, wherein the catalyst used is an aliphatic, cycloaliphatic, or cyclic/aliphatic phosphine oxide.Type: GrantFiled: May 6, 1992Date of Patent: March 23, 1993Assignee: BASF AktiengesellschaftInventors: Jochem Henkelmann, Irene Troetsch-Schaller, Thomas Wettling, Thomas-Michael Kahl, Leopold Hupfer, Wolfgang Franzischka, Hermann Koehler
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Patent number: 5138107Abstract: A process is disclosed for chlorinating, brominating and/or iodinating an organic substrate containing both a single acidic hydrogen atom and at least one electron withdrawing group attached to the same carbon atom. The process replaces the single acidic hydrogen with chlorine, bromine and/or iodine and involves reacting the substrate in solution with a halogenating agent (e.g., a perhalomethane wherein the halogen substituents are I, Br and/or Cl, a trihaloacetic acid ester wherein the halogen substituents are Br and/or Cl, or a perfluoroalkyl halide wherein the halide is I, Br and/or Cl) in the presence of (i) a phase transfer catalyst of the formula R.sup.1 R.sup.2 R.sup.3 R.sup.4 LJ where L is selected from the group consisting of phosphorus and nitrogen, where J is an inorganic anion other than fluoride, and where R.sup.1, R.sup.2, R.sup.3 and R.sup.Type: GrantFiled: July 12, 1991Date of Patent: August 11, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Yoel Sasson
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Patent number: 5099084Abstract: A process is provided for the chlorination of methane using hydrogen chloride as a source of chlorine. The process includes reaction steps operated in tandem in separate zones first comprising the reaction of perchloroethylene with hydrogen chloride and oxygen in the presence of an oxychlorination catalyst to give hexachloroethane and water, and second comprising the vapor phase reaction of hexachloroethane with methane feedstock to produce chlorinated methane, perchloroethylene and hydrogen chloride.Type: GrantFiled: January 13, 1989Date of Patent: March 24, 1992Inventor: John E. Stauffer
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Patent number: 5097083Abstract: A process is provided for the chlorination of ethane using hydrogen chloride, chlorine or mixtures as the chlorinating agent. The process includes reaction steps operated in tandem in separate zones first comprising the reaction of perchloroethylene with hydrogen chloride and oxygen in the presence of an oxychlorination catalyst to give hexachloroethane and water, and second comprising the vapor phase reaction of hexachloroethane with ethane feedstock to produce chlorinated ethanes, chlorinated ethylenes, and hydrogen chloride.Type: GrantFiled: January 13, 1989Date of Patent: March 17, 1992Inventor: John E. Stauffer
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Patent number: 5086178Abstract: Fluorinated diazabicycloalkane derivative of the following Formula I: ##STR1## wherein n represents 0, 1 or 2; R represents a quaternizing organic group; each R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 independently represents hydrogen, C.sub.1 -C.sub.6 alkyl, aryl, C.sub.1 -C.sub.6 alkyl-substituted aryl or aryl-substituted C.sub.1 -C.sub.6 alkyl and each X.sup.- independently represents a conterion or 2X.sup.- represents a single divalent counterion, are electrophilic fluorinating agents.Type: GrantFiled: September 20, 1990Date of Patent: February 4, 1992Assignee: Air Products and Chemicals, Inc.Inventor: Ronald E. Banks
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Patent number: 5025107Abstract: Disclosed is a process for the preparation of bis-acylamido aromatic compounds by reacting certain arylene dihalides with certain arylene dihalides in the presence of a copper catalyst. The process may be utilized in the synthesis of arylenediamines.Type: GrantFiled: July 24, 1989Date of Patent: June 18, 1991Assignee: Eastman Kodak CompanyInventor: Kim S. Chamberlin
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Patent number: 4996371Abstract: The present invention is directed to a method for replacing a carboxylic acid group with a fluorine group in a halogenated aliphatic carboxylic acid compound having the formula, R-COOH, to prepare a fluorinated product having the formula, R-F, wherein R is a halogenated aliphatic group including straight- and branched-chain aliphatic groups selected from the group consisting of halogenated aliphatic and alkoxy-substituted halogenated aliphatic groups, wherein the method comprises the steps of (a) reacting the halogenated aliphatic carboxylic acid compound with bromine trifluoride, and (b) recovering the fluorinated product.Type: GrantFiled: January 16, 1990Date of Patent: February 26, 1991Assignee: BOC, Inc.Inventors: Donald F. Halpern, Mark L. Robin
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Patent number: 4990696Abstract: Perchloroethylene is oxychlorinated to provide hexachloroethane which is reacted with methane to produce methyl chloride which is hydrolyzed to form methyl alcohol product and hydrogen chloride which is recycled to the oxychlorination step.Type: GrantFiled: May 29, 1990Date of Patent: February 5, 1991Inventor: John E. Stauffer
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Patent number: 4978435Abstract: Free chlorine values are removed by radical chlorination from uncombined admixtures thereof, notably admixtures of free chlorine and at least one halogenated organic compound that is not completely chloro-substituted.Type: GrantFiled: August 24, 1988Date of Patent: December 18, 1990Assignee: AtochemInventors: Jean-Jacques Masini, Bertrand Collier
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Patent number: 4954648Abstract: A method for the bromination of aromatic compounds, including substituted deactivated aromatic compounds, at mild temperature conditions is disclosed. The method comprises reacting an aromatic compound with a bromination agent consisting of bromine-trifluoride and bromine at a temperature ranging between -10.degree. C. and 30.degree. C. The bromination reaction takes place instantaneously and the brominated aromatic compound is separated from the original reactant by known organic chemistry techniques.Type: GrantFiled: May 11, 1989Date of Patent: September 4, 1990Assignees: Ramot University Authority of Applied Research and Industrial Development Ltd., ICL Industries Ltd.Inventors: Ori Lerman, Shlomo Rozen
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Patent number: 4948917Abstract: Process for the preparation of .beta.-chloroethylsulfonylaryl isocyanates of the formula (1)Cl--H.sub.2 C--H.sub.2 C--O.sub.2 S--A--NCO (1)wherein A is a phenylene radical, which can contain substituents from the series comprising alkyl(C.sub.1 -C.sub.6), alkoxy(C.sub.1 -C.sub.6), chlorine, bromine and nitro, or a naphthylene radical, by allowing at least 2 moles of phosgene to act on 1 mole of .beta.-hydroxyethylsulfonyl-arylamine of the formula (2)HO--H.sub.2 C--H.sub.2 C--O.sub.2 S--A--NH.sub.2 (2)wherein A has the abovementioned meaning, in the presence of a catalyst at temperatures of about 100.degree. to 200.degree. C., if appropriate in an inert solvent.Type: GrantFiled: February 14, 1990Date of Patent: August 14, 1990Assignee: Hoechst AktiengesellschaftInventor: Hans H. Steuernagel
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Patent number: 4902393Abstract: A process for the production of 1,1,2-trichloro-2-methylpropane comprises reacting 1-chloro-2-methylpropene with sulfuryl chloride. This reaction takes place preferably under the effect of light, especially UV light and/or in the presence of an aldehyde as the catalyst. The starting material contains less than 10 ppm of N-containing compounds conventionally employed to stabilize it.Type: GrantFiled: August 27, 1984Date of Patent: February 20, 1990Assignee: Huels AktiengesellschaftInventor: Dieter J. Muller
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Patent number: 4866200Abstract: Disclosed is a process for the co-production of aromatic carboxylic esters and alkyl iodides by the carbonylation of aromatic iodides in the presence of an alkanol and a palladium catalyst.Type: GrantFiled: August 4, 1988Date of Patent: September 12, 1989Assignee: Eastman Kodak CompanyInventors: Mark Rule, Thomas H. Larkins, Jr., Donald W. Lane, Guy R. Steinmetz
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Patent number: 4851564Abstract: Disclosed is a process for the co-production of aromatic carboxylates and alkyl iodides by the carbonylation of aromatic iodides in the presence of an alkanol and a rhodium catalyst.Type: GrantFiled: February 22, 1988Date of Patent: July 25, 1989Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule
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Patent number: 4847406Abstract: Disclosed is a process for the co-production of aromatic carboxylates and alkyl iodides by the carbonylation of aromatic iodides in the presence of an alkanol and a ruthenium catalyst.Type: GrantFiled: January 12, 1987Date of Patent: July 11, 1989Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule
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Patent number: 4832873Abstract: Polybrominated higher alkylbenzenes may be produced by reacting the corresponding hydrocarbon material with bromine chloride in an excess bromine reaction medium in the presence of an antimony halide catalyst.Type: GrantFiled: October 9, 1987Date of Patent: May 23, 1989Assignee: Great Lakes Chemical CorporationInventors: Nicolai A. Favstritsky, Dennis M. Borden
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Patent number: 4814467Abstract: A process for chlorinating compounds containing a carbon atom bonded to a hetero-atom selected from the group consisting of oxygen, nitrogen and sulfur; said process comprises contacting the carbon hetero-atom containing compound with a chloro phosphorus complex of the formulaRP.sup..sym. CL.sub.3 P.sup..crclbar. Cl.sub.6wherein R is selected from the group consisting of aryl, substituted aryl, alkyl and substituted alkyl, so that the hetero-atom is replaced by at least one chlorine atom; compounds capable of being chlorinated can include, for example, carboxylic acids, acid chlorides, ketones, aldehydes, alcohols, epoxides, esters, anhydrides, ethers, thiols, and aromatic nitro groups; the reaction can be extended to compounds containing the carbon to chlorine bond alpha to a carbon atom containing at least one hydrogen atom, it can be further dehydrochlorinated, e.g., by either heating to a temperature ranging from about 50.degree. C. to about 300.degree. C. or by reaction with a base selected, e.g.Type: GrantFiled: January 22, 1988Date of Patent: March 21, 1989Assignee: ICI Americas Inc.Inventors: Elliott Bay, Andrea Leone-Bay, Peter E. Timony
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Patent number: 4806676Abstract: A process for preparing an aromatic carboxylic ester and an alkyl iodide by carbonylating an aromatic iodide in the presence of an ether, a catalytic amount of a transition metal and a strong acid promoter.Type: GrantFiled: June 20, 1988Date of Patent: February 21, 1989Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule
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Patent number: 4803296Abstract: A process for the co-production of aromatic carboxylic esters and alkyl iodides by the carbonylation of aromatic iodides in the presence of an ether and an iridium catalyst.Type: GrantFiled: May 11, 1988Date of Patent: February 7, 1989Assignee: Eastman Kodak CompanyInventors: Guy R. Steinmetz, Mark Rule, Victor H. Agreda, Lanney C. Treece
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Patent number: 4739057Abstract: A process for converting organic hydroxyl-containing compounds to halides which comprises reacting the hydroxyl-containing compound with a phosphorushalide reagent of formula: R.sub.n PX.sub.5-n wherein n is selected from 1, 2 and 3; R is selected from the group consisting of C-6 to C-10 aryl and substituted aryl wherein the substituents are selected from the group consisting of straight and branched chain alkyl, alkoxy, and haloalkyl, halogen, sulfonate and mixtures thereof; and X is a halogen. It is preferred to carry out the reaction in the presence of an arylphosphorusoxydihalide solvent. The use of an arylphosphorustetrahalide and particularly phenylphosphorustetrachloride is preferred. The arylphoshorustetrahalide can be prepared in situ by contacting a solution of the corresponding arylphosphorusdihalide in an arylphosphorusoxydihalide solvent with a halogen. The process can further comprise the step of heating the reaction mixture. Maintaining a reaction temperature of from about 0.degree. C.Type: GrantFiled: June 30, 1986Date of Patent: April 19, 1988Assignee: Stauffer Chemical Co.Inventors: Andrea Leone-Bay, Elliott Bay, Peter E. Timony
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Patent number: 4734535Abstract: Aliphatic chlorine compounds of the formulaX--R.sup.1 --Cl Iwhere R.sup.1 is alkylene which may be interrupted by one or more oxygen atoms and which may be substituted by halogen, alkyl or aryl, and X is hydrogen, chlorine or OR.sup.2, where R.sup.2 is alkyl, cycloalkyl, aryl or aralkyl, are prepared by decarboxylating chloroformic acid esters or diesters at elevated temperatures by decarboxylating in the presence of a quaternary ammonium or phosphonium salt as catalyst.Type: GrantFiled: March 25, 1987Date of Patent: March 29, 1988Assignee: BASF AktiengesellschaftInventors: Norbert Greif, Knut Oppenlaender
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Patent number: 4714792Abstract: 1,2,3-trichloropropane is prepared by reacting allyl chloride with sulfuryl chloride, in the presence of 1-10,000 ppm of a nitrogen-containing base, a phosphine or a phosphine oxide. Suitable nitrogen-containing bases include aliphatic, aromatic and heterocyclic amines, and mixtures thereof; suitable phosphines are preferably aliphatic or aromatic phosphines and suitable phosphine oxides are aliphatic or aromatic phosphine oxides.Type: GrantFiled: September 6, 1985Date of Patent: December 22, 1987Assignee: Huels AktiengesellschaftInventors: Dieter J. Muller, Heinrich Wehmeyer
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Patent number: 4654449Abstract: Hydrocarbons and other compounds are halogenated to halocarbon products by contact with a halocarbon in the presence of an acidic zeolite catalyst such as ZSM-5. The process is particularly useful for the halogenation of methane to form chemicals of higher value.Type: GrantFiled: December 9, 1982Date of Patent: March 31, 1987Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, Patrick D. Perkins
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Patent number: 4532347Abstract: The instant invention relates to a membrane solvent extraction and reaction system. More particularly it pertains to an improvement in the membrane solvent extraction system wherein a solute is extracted through a polymeric membrane from one solvent liquid phase to an extracting solvent liquid without direct contact between the liquid phases which are separated by the membrane and in which the extracting solvent has no greater solubility and usually substantially less solubility for the solute than the feed solvent. The impovement comprises converting the solute permeating across the membrane to a different chemical compound, whereby a high concentration gradient for the solute across the membrane is maintained to improve the separation of the solute from the feed solvent liquid phase.Type: GrantFiled: January 21, 1980Date of Patent: July 30, 1985Assignee: Varen TechnologyInventor: Ronald J. Vaughan
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Patent number: 4518813Abstract: (2R,6R)-1-Chloro-2,6,10-trimethyl-undecane I, (R)-(+)-.beta.-chloro-isobutyric acid II, (S)-(+)-1-bromo-3-chloro-2-methylpropane IV and (2R)-(+)-1-chloro-2,6-dimethyl-heptane V are novel optically active units for the synthesis of the side chain of (R,R,R)-.alpha.-tocopherol. In the process according to the invention, the optically active C.sub.Type: GrantFiled: September 30, 1982Date of Patent: May 21, 1985Assignee: BASF AktiengesellschaftInventors: Hansgeorg Ernst, Friedrich Vogel, Joachim Paust
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Patent number: 4475003Abstract: 1,1,1-Trichloromethyl compounds are prepared by a process in which chloroform is reacted with an olefin in the presence of a free-radical initiator and of a weakly basic alkali metal salt or alkaline earth metal salt, and are useful intermediates for the preparation of dyes, drugs and pesticides.Type: GrantFiled: September 13, 1982Date of Patent: October 2, 1984Assignee: BASF AktiengesellschaftInventor: Martin Fischer
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Patent number: 4413137Abstract: Vicinal epoxides and an alkylene dihalide are prepared by contacting a mixture comprising ethylene carbonate and a .beta.-haloalkyl carbonate with an initiator at a temperature from about 25.degree. C. to about 260.degree. C.Type: GrantFiled: June 21, 1982Date of Patent: November 1, 1983Assignee: The Dow Chemical CompanyInventors: James M. Renga, Roy A. Periana-Pillai
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Patent number: 4409198Abstract: Copper(II) chloride is prepared from copper(II) oxychloride in a nonpolar solvent, preferably during oxychlorination. As the source of hydrogen chloride, the hydrochlorides of certain tertiary amines having 12-40 carbon atoms in total are utilized. The amine contains at most one N-methyl group and its dissociation constant K.sub.a of the equilibrium reactionNR.sub.3 H.sup..sym. +H.sub.2 O.revreaction.NR.sub.3 +H.sub.3 O.sup..sym.is 10.sup.-3.5 to 10.sup.-8.5. Preferred tertiary amines are a trialkylamine of 15-36 carbon atoms; an N-alkylazacycloalkane of the formula ##STR1## wherein R is alkyl of 6-15 carbon atoms, 5.ltoreq.n.ltoreq.8, ALK represents one or more alkyl substituents, and the N-alkylazacycloalkane contains at least 15 carbon atoms; or an N,N-dialkylaniline wherein each alkyl group independently contains 6-12 carbon atoms and the benzene ring is optionally substituted by one or more alkyl groups of 1-3 carbon atoms each.Type: GrantFiled: August 4, 1982Date of Patent: October 11, 1983Assignee: Chemische Werke Huls, AGInventors: Alfred Coenen, Manfred Schroeder, Guenter Prominski
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Patent number: 4366324Abstract: The invention provides a novel continuous process for concurrently producing methyl chloride and organosiloxanes by the reaction of an organochlorosilane and methyl alcohol in an aqueous reaction medium at 70.degree. to 150.degree. C. Different from conventional processes, the aqueous reaction medium contains no catalyst so that the problems inherent to the use of a large amount of a catalyst can be avoided. In the inventive process, the feed rates of the reactants are controlled so as to keep the concentration of hydrogen chloride in the aqueous reaction medium not to exceed the azeotropic concentration thereof at the temperature and under the pressure of operation. These conditions are critical to reduce the loss of hydrogen chloride by dissipation into the gaseous phase resulting in a remarkably high yield of methyl chloride from the standpoint of both the conversion of chlorine content and the space-time yield of the reaction vessel.Type: GrantFiled: November 18, 1981Date of Patent: December 28, 1982Assignee: Shin-Etsu Chemical Co. Ltd.Inventors: Kiichi Habata, Kesazi Ichikawa, Mutsuo Shimizu
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Patent number: 4362884Abstract: Organosilicon compounds referred to as silacrown ethers or "silacrowns" are of the general formula: ##STR1## where R.sup.1 and R.sup.2 are organic radicals or hydrogen and n is an integer between 4 and 10 inclusive. Silacrown ethers are prepared by reacting polyethylene glycol with substituted silanes under conditions promoting cyclization over polymerization. Silacrown ethers may be employed as phase-transfer catalysts in solution or immobilized on siliceous supports.Type: GrantFiled: November 23, 1981Date of Patent: December 7, 1982Assignee: Petrarch Systems, Inc.Inventor: Barry C. Arkles
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Patent number: 4351972Abstract: The invention relates to the production of anhydrous alkyl iodides. To this end, carboxylic acid alkyl esters of the formula R.sup.1 COOR.sup.2, in which R.sup.1 stands for hydrogen or an alkyl or aryl radical having from 1 to 8 carbon atoms and R.sup.2 stands for an alkyl group having from 1 to 4 carbon atoms, are reacted with iodine and hydrogen and optionally with carbon monoxide in the presence of compounds of noble metals comprised of rhodium, iridium, palladium or ruthenium as catalyst, and of a heterocyclic aromatic compound, in which at least one hetero atom is a quaternary nitrogen atom, or of a quaternary organophosphorus compound as a promoter, and optionally also in the presence of a carboxylic acid having from 1 to 8 carbon atoms and/or its anhydrides. The reaction is effected under practically anhydrous conditions at temperatures of from 350 to 420 K. and under a total pressure of up to 30 bars.Type: GrantFiled: August 26, 1981Date of Patent: September 28, 1982Assignee: Hoechst AktiengesellschaftInventors: Hans K. Kubbeler, Heinz Erpenbach, Klaus Gehrmann, Klaus Schmitz
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Patent number: 4322355Abstract: An improvement in the reaction of olefin with aldehyde, and optionally, carboxylic acid, in the liquid phase in the presence of a catalytically effective amount of strong acid to provide a 1,3-difunctional compound or a mixture of 1,3-difunctional compounds is provided by carrying out the aforesaid reaction in the further presence of a co-catalyst selected from the group consisting of antimony oxide, bismuth oxide, antimony salt, bismuth salt and mixtures thereof.Type: GrantFiled: April 15, 1980Date of Patent: March 30, 1982Assignee: National Distillers & Chemical Corp.Inventors: David Horvitz, William D. Baugh
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Patent number: 4306100Abstract: Alkenediols are produced by hydrolysis of a dibromoalkenes in the presence of alkali metal formate. In a preferred embodiment, alkenediols, and particularly 2-butene-1,4-diol, are produced in a series of steps comprising bromination of conjugated diene with cupric bromide, hydrolysis of the resulting dibromobutenes to alkenediols in the presence of alkali metal formate, and regeneration of cupric bromide and alkali metal formate such that only conjugated diene, oxygen and water are consumed.Type: GrantFiled: June 16, 1980Date of Patent: December 15, 1981Assignee: Standard Oil Company (Indiana)Inventor: George R. Wood
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Patent number: 4305876Abstract: A process for asymmetrically hydrogenating through the use of microorganisms a double bond connected to tertiary carbon atom in an olefinic aliphatic compound to produce a tertiary, optically active aliphatic compound useful as an intermediate for optically active Vitamins E and K.Type: GrantFiled: November 24, 1978Date of Patent: December 15, 1981Assignee: Hoffmann-La Roche, Inc.Inventors: Richard Barner, Walter Boguth, Hans G. W. Leuenberger, Max Schmid, Reinhard Zell
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Patent number: RE35568Abstract: The present invention is directed to a method for replacing a carboxylic acid group with a fluorine .[.group.]. in a halogenated aliphatic carboxylic acid compound having the formula, R-COOH, to prepare a fluorinated product having the formula, R-F, wherein R is a halogenated aliphatic group including straight- and branched-chain aliphatic groups selected from the group consisting of halogenated aliphatic and .Iadd.halogenated .Iaddend.alkoxy-substituted .[.halogenated.]. aliphatic groups, wherein the method comprises the step of (a) reacting the halogenated aliphatic carboxylic acid compound with bromine trifluoride, and (b) recovering the fluorinated product.Type: GrantFiled: November 16, 1994Date of Patent: July 22, 1997Assignee: Ohmeda Pharmaceutical Products Division Inc.Inventors: Donald F. Halpern, Mark L. Robin