Preparing By Reacting Hydrogen Halide With A Compound Which Contains Hydroxy Bonding Directly To Carbon Patents (Class 570/258)
-
Patent number: 10138174Abstract: Ethylene is produced from ethanol in a one-step process by reacting ethanol with hydrogen chloride over a catalyst composed of silica alumina catalyst in intimate admixture with activated charcoal.Type: GrantFiled: December 29, 2017Date of Patent: November 27, 2018Inventor: John E. Stauffer
-
Patent number: 9234682Abstract: A two-phase heat exchanger includes a hot side heat sink, a cold side heat sink, and one or more thermoelectric modules disposed between the hot side heat sink and the cold sink heat sink such that hot sides of the one or more thermoelectric modules are thermally coupled to the hot side heat sink and cold sides of the one or more thermoelectric modules are thermally coupled to the cold side heat sink. The two-phase heat exchanger is configured to be mounted at an angle from vertical.Type: GrantFiled: May 7, 2013Date of Patent: January 12, 2016Assignee: Phononic Devices, Inc.Inventors: Jesse W. Edwards, M. Sean June, Robert Joseph Therrien, Abhishek Yadav
-
Publication number: 20150031926Abstract: Methods and assemblies for improving the reaction kinetics of, conserving reactants utilized in, and/or producing a more pure reaction product of, liquid-phase reactions that involve volatile reactants and products are provided. The methods and assemblies herein provide for a feed of reaction liquid to two or more absorption zones, wherein the temperature and/or feed rate of the liquid is independently adjusted prior to introduction into at least one of the two or more absorption zones. More particularly, the temperature and feed rate of the liquid as delivered to each absorption zone can be adjusted independently to optimize the absorption of at least a portion of any gaseous reactants and byproducts from the gaseous product stream and/or to optimize reaction zone conditions. Reaction kinetics may thus be improved, or substantially maintained.Type: ApplicationFiled: October 13, 2014Publication date: January 29, 2015Applicant: DOW GLOBAL TECHNOLOGIES LLCInventor: John D. Myers
-
Patent number: 8859830Abstract: Methods and assemblies for improving the reaction kinetics of, conserving reactants utilized in, and/or producing a more pure reaction product of, liquid-phase reactions that involve volatile reactants and products are provided. The methods and assemblies herein provide for a feed of reaction liquid to two or more absorption zones, wherein the temperature and/or feed rate of the liquid is independently adjusted prior to introduction into at least one of the two or more absorption zones. More particularly, the temperature and feed rate of the liquid as delivered to each absorption zone can be adjusted independently to optimize the absorption of at least a portion of any gaseous reactants and byproducts from the gaseous product stream and/or to optimize reaction zone conditions. Reaction kinetics may thus be improved, or substantially maintained.Type: GrantFiled: March 4, 2010Date of Patent: October 14, 2014Assignee: Dow Global Technologies Inc.Inventor: John D. Myers
-
Patent number: 8664424Abstract: Provided is a method for preparing 2,5-dimethylphenylacetic acid, wherein p-xylene is mixed with paraformaldehyde and concentrated hydrochloric acid in a solvent of ion liquid to obtain 2,5-dimethyl benzyl chloride by the chloromethylation reaction. Then, 2,5-dimethyl benzyl chloride is introduced into a reactor with an acid binding agent and a solvent, the carbonylation and hydrolysis reaction is conducted in the presence of a catalyst to obtain 2,5-dimethylphenylacetic acid. The present process has new route, less synthesis steps, simple operation, lower cost, increased yield, and is friendly to the environment. Therefore, the method is suitable for industrial production.Type: GrantFiled: June 7, 2011Date of Patent: March 4, 2014Assignees: Lianhe Chemical Technology Co., Ltd, Jiangsu Lianhe Chemical Technology Co., Ltd.Inventors: Ping Wang, Xiaobin Fan, Xingjun Lin, Zhaohui He
-
Publication number: 20110060173Abstract: Methods and assemblies for improving the reaction kinetics of, conserving reactants utilized in, and/or producing a more pure reaction product of, liquid-phase reactions that involve volatile reactants and products are provided. The methods and assemblies herein provide for a feed of reaction liquid to two or more absorption zones, wherein the temperature and/or feed rate of the liquid is independently adjusted prior to introduction into at least one of the two or more absorption zones. More particularly, the temperature and feed rate of the liquid as delivered to each absorption zone can be adjusted independently to optimize the absorption of at least a portion of any gaseous reactants and byproducts from the gaseous product stream and/or to optimize reaction zone conditions. Reaction kinetics may thus be improved, or substantially maintained.Type: ApplicationFiled: March 4, 2010Publication date: March 10, 2011Applicant: DOW GLOBAL TECHNOLOGIES INC.Inventor: John D. Myers
-
Publication number: 20100234653Abstract: The invention is directed to processes for producing an alkyl halide, preferably isobutyl bromide. In one embodiment, the process comprises the steps of: (a) contacting an alcohol with a hydrogen halide in a reactor at elevated temperature under conditions effective to form an initial product mixture comprising the alkyl halide, the alcohol, the hydrogen halide and water; (b) cooling the initial product mixture to form a cooled organic phase positioned above a cooled aqueous phase; (c) separating the cooled organic phase from the cooled aqueous phase. The process preferably further comprises a step of: (d) heating at least a portion of the cooled aqueous phase under conditions effective to form additional alkyl halide.Type: ApplicationFiled: March 12, 2009Publication date: September 16, 2010Applicant: Chemtura CorporationInventors: Mitchel Cohn, Steven J. Hobbs
-
Patent number: 7652180Abstract: The invention relates to a process for preparing alkyl chlorides by reacting alcohols with gaseous hydrogen chloride in the presence of a catalyst, wherein the catalyst comprises at least one compound of the structure: wherein R1 is a linear alkyl group having from 1 to 20 carbon atoms, R2, R3, and R4 is selected from a hydrogen, an alkyl, an alkenyl, an aralkyl or an alkylaryl group from 1 to 20 carbon atoms, wherein the substituents of R2, R3, and R4 are all identical, are all different or two of the substituents of R2, R3, and R4 type are identical.Type: GrantFiled: February 23, 2006Date of Patent: January 26, 2010Assignee: Degussa AGInventors: Clemens Osterholt, Manfred Neumann, Thomas Kuebelbaeck, Kerstin Bodmann
-
Patent number: 7304192Abstract: The present invention relates to a simple method for efficiently producing aromatic-substituted chlorinated hydrocarbons, for example, high-purity cumyl chloride (1,4-bis(1-chloro-1-methylethyl)benzene, p-DCC) that can be used as an initiator for cationic polymerization. A corresponding tertiary alcohol such as 1,4-bis(1-hydroxy-1-methylethyl)benzene is mixed with aqueous hydrochloric acid and subjected to stirring, and then the resulting organic layer is brought into contact with a hydrogen chloride gas to produce high-quality aromatic-substituted chlorinated hydrocarbon in high yield. Furthermore, in order to purify a mixture containing a chlorinated hydrocarbon compound, the mixture being produced by reaction between an aqueous solution of a metal hypochiorite and a protonic acid, the mixture is allowed to react with an aqueous alkaline solution to form an alcohol compound. Then, a solid is isolated by solid-liquid separation and chlorinated again with the aqueous hydrochloric acid.Type: GrantFiled: July 2, 2003Date of Patent: December 4, 2007Assignee: Kaneka CorporationInventors: Takeshi Kawamura, Chiho Yoshimi, Hidetoshi Odaka
-
Patent number: 6992038Abstract: The present invention is to solve the problems caused by a conventional method for producing a zinc chloride-loaded support wherein zinc chloride is adsorbed on a solid support in an aqueous solution of zinc chloride. The problems include environmental destruction caused by the treatment of a used aqueous solution of zinc chloride, corrosion to a reactor, a threat to health for workers, deterioration of zinc chloride due to deliquescence thereof, and reduction of specific surface area.Type: GrantFiled: November 18, 2003Date of Patent: January 31, 2006Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Mitsuo Narita, Masaki Tabata, Kazuhisa Hayakawa
-
Patent number: 6989175Abstract: A method for the acyl fluoride activation of a carboxysilyl-coated glass is described. The method includes providing a glass substrate having a surface with at least one pendant carboxysilyl linker comprising a carboxyl group and activating without etching the surface of the glass by converting the carboxyl group into an acyl fluoride group. In one embodiment, the surface of the glass may be activated by contacting the surface with a fluoridating agent and a tertiary amine reagent, and a solvent that is capable of binding hydrogen fluoride. A substrate for the covalent immobilization of nucleophile-containing species is also provided. The substrate comprises a glass having a surface with a pendant carboxysilyl linker activated by acyl fluoride without etching the surface of the glass. The invention also provides a bioarray formed on a glass surface activated with acyl fluorides without etching.Type: GrantFiled: March 8, 2002Date of Patent: January 24, 2006Assignee: Beckman Coulter, Inc.Inventor: Raymond C. Milton
-
Patent number: 6414204Abstract: In a process for production of allyl chloride whereby allyl alcohol and hydrogen chloride are reacted in the presence of a catalyst and the resulting allyl chloride is distilled off from the reaction system, the by-production of diallyl ether is suppressed by lowering the molar concentration ratio of hydrogen chloride with respect to allyl alcohol in the reaction solution ([AAL]½/[HCL]).Type: GrantFiled: February 15, 2001Date of Patent: July 2, 2002Assignee: Showa Denko K.K.Inventors: Kenji Usui, Shoichi Oishi, Toshitaka Hiro, Tatsuharu Arai
-
Patent number: 6326519Abstract: Diallylic sulfides represented by Formula I wherein: R1 and R2 are independently chosen from the group consisting of —CHO, —CH2Cl, —CH2Br, —CH2I, —CH2OH, CH2OSO2CF3, —CH2OSO2Ph, —CH2OSO2C6H4CH3 and —CH2OSO2CH3 and processes for making the same.Type: GrantFiled: June 4, 2001Date of Patent: December 4, 2001Inventors: Sangho Koo, Hojin Choi, Minsoo Park, Minkoo Ji
-
Patent number: 6206819Abstract: N,N-disubstituted formamides, wherein the substituents are selected to provide formamides which have low volatility, are useful as halogenation catalysts. Such catalysts are generally less hazardous to use than typical formamide halogenation catalysts because toxic catalyst by-products are also less volatile. Methods for using such catalysts are provided.Type: GrantFiled: May 15, 2000Date of Patent: March 27, 2001Assignee: Rohm and Haas CompanyInventors: Deborah Diane Graves, Thomas Duncan Rose, David James Swank, Charles Chao Wu
-
Patent number: 6111153Abstract: A process for manufacturing methyl chloride. The process consists essentially of contacting hydrogen chloride with at least a stoichiometric amount of methanol split into at least two portions with a first portion comprising about 60 to 95 percent of the methanol added to the process in the presence of a first liquid medium at a temperature in the range of about 115.degree. C. to 170.degree. C. to form a gaseous mixture containing methyl chloride, and contacting the gaseous mixture with a second methanol portion and adding to a second liquid medium at a temperature in the range of about 100.degree. C. to 160.degree. C., and recovering the methyl chloride.Type: GrantFiled: June 1, 1999Date of Patent: August 29, 2000Assignees: Dow Corning Corporation, Dow Corning LimitedInventors: Robert Dennis Crow, Neil Philip Roberts
-
Patent number: 6077981Abstract: Disclosed is a process for the production of cyclopropylmethyl halides (CPMX) such as cyclopropylmethyl chloride (CPMCl) and cyclopropylmethyl bromide (CPMBr) wherein cyclopropanemethanol (CPMO) is contacted with an aqueous solution of a hydrogen halide (HX) at a temperature in the range of -30.degree. C. to 35.degree. C. Also disclosed is a three-step process wherein CPMO is converted to a CPMX, the CPMX is separated as a liquid organic phase from the aqueous hydrogen halide by decantation and then is subjected to fractional distillation to provide CPMX in high purity. Finally, a process for the co-production of a CPMX and a cyclobutyl halide (CBX) is disclosed.Type: GrantFiled: August 28, 1998Date of Patent: June 20, 2000Assignee: Eastman Chemical CompanyInventors: Shaowo Liang, Colin Henry Ridyard, Daniel Latham Terrill, Clyde Neil Clubb
-
Patent number: 5917099Abstract: Methyl chloride is prepared by effecting liquid-phase reaction between hydrogen chloride and methanol in the absence of a catalyst. The reaction is effected in divided stages including at least an early stage and a last stage. The early stage of reaction is effected in a stoichiometric excess of hydrogen chloride. The last stage of reaction is effected in a stoichiometric excess of methanol. The invention is industrially advantageous in that methyl chloride can be prepared at a high conversion of hydrogen chloride while suppressing the formation of dimethyl ether by-product.Type: GrantFiled: May 14, 1998Date of Patent: June 29, 1999Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tomomi Narita, Hiroyuki Kobayashi, Yukinori Satoh, Yoshihiro Shirota
-
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
-
Patent number: 5859070Abstract: Synthesis of small quantities of compounds such as methanol from reagents, especially radio-labelled reagents such as .sup.11 C oxides, in a carrier gas by a catalytic reaction using a catalyst that has been pre-conditioned for the reaction by previous use for the desired reaction and has then been passivated, or has been maintained in the pre-conditioned state, until contacted with said carrier gas. Where the product is adsorbed by the catalyst, it may be desorbed by heating or displaced by contacting the catalyst with a material, e.g. a catalyst poison that is more strongly adsorbed. Such a more strongly adsorbed material may react with the adsorbed catalytic product to produce a desired product.Type: GrantFiled: July 22, 1996Date of Patent: January 12, 1999Assignee: Imperial Chemical Industries, PLCInventors: Samuel David Jackson, Frederick Ernest Hancock, Bernard John Crewdson
-
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
-
Patent number: 5767330Abstract: The preparation of long-chain alkyl chlorides from alcohols and hydrogen chloride is improved by carrying out the reaction at a temperature below the boiling point of the alkyl chloride, and distilling off the resulting alkyl chloride by feeding in additional hydrochloric acid.Type: GrantFiled: February 10, 1997Date of Patent: June 16, 1998Assignee: Huels AktiengesellschaftInventors: Josef Metz, Clemens Osterholt, Juergen Lange
-
Patent number: 5763712Abstract: This invention relates to a process for the preparation and fractionation of a mixture of dimethyl ether and chloromethane by extractive distillation with methanol as extractant. The mixture is prepared by reacting methanol with hydrogen chloride. The mixture is then distilled to remove water and is subsequently subjected to an extractive distillation with methanol as extractant, with chloromethane resulting as top product. In another distillation step, the remaining dimethyl ether is separated from the methanol.Type: GrantFiled: June 23, 1997Date of Patent: June 9, 1998Assignee: Hoechst AktiengesellschaftInventors: Peter Roth, Erhard Leistner, Wolfgang Wendel
-
Patent number: 5723704Abstract: Process for the preparation of alkyl chlorides, characterized in that:a) in a first stage a primary mono- or polyhydric alcohol, which has a C.sub.4 -C.sub.30 carbon chain which is saturated, substituted or otherwise by one or more chlorine atoms and branched or otherwise and which may comprise one or more C.sub.5 -C.sub.7 cycloalkyl groups, is reacted with gaseous hydrochloric acid in the absence of catalyst and at a temperature of between 80.degree. C. and 170.degree. C., until the degree of conversion of the alcohol functional groups is equal to or between 60 and 95 mol %, andb) in a second stage phosgene and a catalyst are introduced into the reaction mixture, the catalyst being chosen from the group consisting of hexaalkylguanidinium halides and their hydrohalides, quaternary ammonium halides, quaternary phosphonium halites, pyridine and pyridines substituted by one or more C.sub.1 -C.sub.6 alkyl groups, at a temperature of between 80.degree. C. and 160.degree.C.Type: GrantFiled: January 3, 1997Date of Patent: March 3, 1998Assignee: Societe Nationale des Poudres et ExplosifsInventors: Herve Demail, Jean-Claude Schweickert, Pierre Le Gars
-
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
-
Patent number: 5436378Abstract: Water-containing mixtures of at least one hydrocarbon/halocarbon and hydrochloric acid, e.g., the methyl chloride feedstream in conventional process for the synthesis of chloromethanes, are desiccated by intimately contacting such mixtures with an effective drying amount of an essentially anhydrous drying agent that includes (i) a metal sulfate, chloride or perchlorate, or (ii) phosphorus pentoxide.Type: GrantFiled: June 21, 1994Date of Patent: July 25, 1995Assignee: AtochemInventors: Jean-Jacques Masini, Elie Ghenassia, Raymond Commandeur, Rene Clair, Jean-Louis Guillaumenq
-
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
-
Patent number: 5321171Abstract: A method for producing methyl chloride, which comprises reacting methanol and hydrogen chloride in a gas phase in the presence of a catalyst, wherein a zirconium oxide catalyst or a composite catalyst comprising at least two oxides of metals selected from the group consisting of Zr, Ti and Al, is used as the catalyst.Type: GrantFiled: June 18, 1993Date of Patent: June 14, 1994Assignee: Asahi Glass Company Ltd.Inventors: Takeshi Morimoto, Shinsuke Morikawa, Hirokazu Takagi, Naoki Yoshida
-
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
-
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
-
Patent number: 5202512Abstract: Process for the preparation of methyl chloride, which comprises reacting methanol with hydrogen chloride in a concentration below the particular ageotropic concentration in the liquid phase in the presence of an amine hydrohalide.Type: GrantFiled: February 3, 1992Date of Patent: April 13, 1993Assignee: Wacker-Chemie GmbHInventors: Peter-Paul Winkler, Ulrich Goetze
-
Patent number: 5196618Abstract: An improvement is proposed in the method for the preparation of methyl chloride from carbon tetrachloride and methyl alcohol by the reaction including the partial reactions of, first, the hydrolysis reaction of carbon tetrachloride with water to form hydrogen chloride and carbon dioxide and, second, the reaction of methyl alcohol with hydrogen chloride, each in the presence of a solid catalyst of zinc chloride supported on active carbon. The uncontrollable temperature increase when these reactions are performed on a single catalyst bed can be avoided by conducting the first partial reaction in a first reaction zone with a feed of carbon tetrachloride and water alone and the second partial reaction is conducted in a separate second reaction zone into which the gaseous mixture from the first zone and methyl alcohol are introduced.Type: GrantFiled: February 28, 1992Date of Patent: March 23, 1993Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Toshihiro Okon, Takaaki Shimizu
-
Patent number: 5138110Abstract: A process for preparing lower alkyl-halides from the reaction of HX and the corresponding lower alcohol, wherein X represents a halogen atom, comprises continuously feeding HX and a lower alcohol to a reactor maintaining the instantaneous molar ratio of HX to the alcohol greater than 3, and continuously distilling off lower alkyl-halide and water from the reactor, continuously separating the lower alkyl-halide and water and recycling part of the said water to the distillation column to abate HX distillation from the reactor. High acid concentration and temperatures are maintained to obtain high yields and rapid conversion of alkanols.Type: GrantFiled: August 13, 1991Date of Patent: August 11, 1992Assignee: Bromine Compounds Ltd.Inventors: Jeane Segall, Leonard M. Shorr
-
Patent number: 5132476Abstract: The vaporous reaction product from the continuous reaction of C.sub.3 -C.sub.4 monoalkanols with hydrogen chloride is removed, condensed, and split into a light organic phase and a heavy aqueous phase. The heavy aqueous phase is immediately distilled yielding HCl-containing reaction water at the bottom of the column and an alcohol stream at the head of the column from where it is returned to the synthesis. The light organic phase is washed with water, dried and, optionally, distilled. The water from this washing operation is neutralized, stripped off in order to remove dissolved organic constituents, and removed as waste water from the system.Type: GrantFiled: June 24, 1991Date of Patent: July 21, 1992Assignee: RWE-DEA Aktiengesellschaft fuer Mineraloel und ChemieInventors: Gunther Osterburg, Wolfgang Reith, Karl-Heinz Gluzek
-
Patent number: 5109138Abstract: A process for hydrohalogenating methanol with a hydrogen halide using a catalyst having an initial zone of lower activity and subsequent zones of higher activity so that coke formation and pressure drop are decreased and catalyst life is increased while overall high catalyst activity is maintained. One example of such a process uses a low surface area amorphous alumina in an initial zone and then progressively higher surface area alumina in subsequent zones.Type: GrantFiled: May 14, 1991Date of Patent: April 28, 1992Assignee: The Dow Chemical CompanyInventors: Michael T. Holbrook, Lawrence A. Hebert, Stephen W. Najmy, Ernest F. Stine, Jr., Reimer Hasche
-
Patent number: 4935564Abstract: A process for preparation of an alkyl halide, RX, from reaction between the corresponding alcohol, ROH, and a hydrogen halide, HX, which improves conversion of the hydrogen halide to the alkyl halide in a single pass through a reactor. The process comprises (A) contacting and reacting the hydrogen halide with a stoichiometric excess of the alcohol in a plug-flow reactor in which flow of a mixture comprising unreacted alcohol, unreacted hydrogen halide, the alkyl halide, and water is co-current; and (B) isolating and separating the alkyl halide.Type: GrantFiled: July 28, 1988Date of Patent: June 19, 1990Assignee: Dow Corning CorporationInventors: Timothy R. Bunce, Ronald S. Evanko, Timothy G. Hueston
-
Patent number: 4935565Abstract: Methyl chloride is produced by contacting methanol and hydrogen chloride in the vapor phase in the presence of KZnCl.sub.3 supported on silica. The process produces methyl chloride in good yield with minimal formation of dimethyl ether as a by-product.Type: GrantFiled: August 24, 1988Date of Patent: June 19, 1990Assignee: The Dow Chemical CompanyInventors: A. Dale Harley, Michael T. Holbrook
-
Patent number: 4922043Abstract: In a process for making methyl chloride by the catalytic hydrochlorination of methanol in the liquid phase, the common formation of unwanted dimethyl ether by-product is reduced by conducting the process in at least two reactors operating in series and by introducing all or substantially all of the required hydrogen chloride feed into the first reactor while splitting the introduction of methanol feed, preferably as a vapor, between or among the reactors.The overall feed ratio of methanol to hydrogen chloride is in the range between about 0.65 to about 1.0 mol methanol per mol hydrogen chloride. Aqueous zinc chloride is the preferred catalyst.Type: GrantFiled: December 2, 1988Date of Patent: May 1, 1990Assignee: Vulcan Materials CompanyInventor: Jimmy T. Petrosky
-
Patent number: 4808761Abstract: Residual aqueous phases, emanating from the synthesis of methyl chloride by reacting methanol with hydrochloric acid, are conveniently demethanolized by maintaining same in liquid phase and in the absence of catalyst, at a temperature of from 50.degree. to 150.degree. C. and under a pressure of less than about 8 bars. The methanol recovered is in the form of a crude methyl chloride which is advantageously recycled to the CH.sub.3 OH/HCl reaction zone.Type: GrantFiled: October 1, 1986Date of Patent: February 28, 1989Assignee: AtochemInventors: Bernard Durand, Jean-Jacques Masini
-
Patent number: 4794204Abstract: A process is described for the removal of dimethyl ether in methyl chloride by catalytic cleavage by means of hydrogen chloride. Dimethyl ether is present as an impurity in crude methyl chloride produced by the catalytic esterification of methanol. The crude methyl chloride is cooled so that water and hydrogen chloride separate out. Gaseous hydrogen chloride is then added to the methyl chloride in an amount corresponding to at least twice the molar amount of dimethyl ether, and the gaseous mixture is passed over a methanol esterification contact catalyst at an elevated temperature.Type: GrantFiled: June 11, 1987Date of Patent: December 27, 1988Assignee: Hoechst AktiengesellschaftInventors: Hendrik W. Post, Helmold von Plessen, Wilhelm Lendle
-
Patent number: 4465880Abstract: Methyl chloride is manufactured from methanol and hydrogen chloride in the gaseous phase in the presence of an aluminum oxide catalyst. The reaction is carried out in the presence of from 1 to 80 liters of oxygen per kg of methanol.Type: GrantFiled: April 24, 1981Date of Patent: August 14, 1984Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Grunbein, Wilhelm Lendle, Hendrik W. Post, Heinz Richter, Manfred Rossberg
-
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